Aqua­(4-methyl­quinoline-κN)[N-(2-oxidobenzyl­idene)glycinato-κ3O,N,O′]copper(II) hemihydrate

Trávníček, Z.; Marek, J.; Vančo, J.; Švajlenová, O.

doi:10.1107/S1600536807067852

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Pages m282-m283

doi:10.1107/S1600536807067852

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Aqua(4-methylquinoline-κN)[N-(2-oxidobenzylidene)glycinato-κ³O,N,O′]copper(II) hemihydrate

Zdeněk Trávníček,^a ^* Jaromír Marek,^a,^b Ján Vančo ^a,^c and Oľga Švajlenová ^d

^aDepartment of Inorganic Chemistry, Faculty of Science, Palacký University, Křížkovského 10, CZ-771 47 Olomouc, Czech Republic, ^bLaboratory of Functional Genomics and Proteomics, Institute of Experimental Biology, Faculty of Science, Masaryk University, Kamenice 5, CZ-625 00 Brno, Czech Republic, ^cDepartment of Chemical Drugs, Faculty of Pharmacy, Palackého 1/3, CZ-612 42 Brno, Czech Republic, and ^dDepartment of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, Kalinčiakova 8, SK-832 32 Bratislava, Slovak Republic
^*Correspondence e-mail: zdenek.travnicek@upol.cz

(Received 15 December 2007; accepted 20 December 2007; online 4 January 2008)

The title complex, [Cu(C₉H₇NO₃)(C₁₀H₉N)(H₂O)]·0.5H₂O, crystallizes with two independent formula units in the asymmetric unit; the solvent molecule is located on a twofold axis of symmetry. The Cu^II atom is coordinated by one tridentate N-salicylideneglycinate Schiff base ligand, one 4-methylquinoline ligand and one water molecule, leading to a slightly distorted square-pyramidal N₂O₃ geometry. In the crystal structure, the molecules are linked by O—H⋯O hydrogen bonds into linear chains in the [100] direction. The structure is further stabilized by intermolecular C—H⋯O interactions and C⋯C contacts with C⋯C = 3.3058 (2), 3.3636 (2) and 3.3946 (2) Å.

Related literature

For synthesis, see: Kishita et al. (1964 ). For related literature, see: Katsuki (2003 ); Vančo et al. (2004 , 2008 ); Bauerová et al. (2005 ). For related structures, see: Valent et al. (2002 ); Warda (1998a ,b ,c ,d ).

Experimental

Crystal data

[Cu(C₉H₇NO₃)(C₁₀H₉N)(H₂O)]·0.5H₂O
M_r = 410.9
Monoclinic, P 2/c
a = 10.0966 (7) Å
b = 12.3483 (6) Å
c = 28.8133 (17) Å
β = 97.730 (6)°
V = 3559.7 (4) Å³
Z = 8
Mo Kα radiation
μ = 1.26 mm⁻¹
T = 120 (2) K
0.30 × 0.25 × 0.25 mm

Data collection

Kuma KM-4-CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Versions 1.171.31.7. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.690, T_max = 0.729
19645 measured reflections
6242 independent reflections
4225 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.113
S = 1.09
6242 reflections
499 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4V⋯O102ⁱ	0.879 (19)	1.88 (2)	2.756 (4)	174 (4)
O4—H4W⋯O2ⁱⁱ	0.87 (4)	2.01 (3)	2.825 (4)	155 (4)
O5—H5V⋯O101ⁱⁱⁱ	0.890 (19)	1.99 (2)	2.865 (4)	169 (4)
O6—H6V⋯O1	0.876 (19)	2.01 (2)	2.867 (4)	165 (4)
O104—H4Y⋯O2	0.879 (19)	1.90 (2)	2.751 (4)	162 (4)
O104—H4Z⋯O102ⁱⁱⁱ	0.87 (4)	1.98 (2)	2.823 (4)	162 (4)
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Versions 1.171.31.7. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Versions 1.171.31.7. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067852/tk2236sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807067852/tk2236Isup2.hkl

checkCIF report

Comment top

Schiff bases, as condensation products of carbonyls and amines, and their coordination compounds find their utilization in different branches of chemical technology (Katsuki, 2003) and participate in some biochemical pathways, e.g. transamination processes, catalyzed by metalloenzymes.

In connection with our recent studies on copper and zinc salicylidene-derived Schiff base complexes, we report now the structure of (I). The Schiff base (Salgly) ligand represents a condensation product of salicylaldehyde and glycine. The title complex, in the form of an anhydrous compound, showed significant microbistatic and fungistatic effects (Valent et al., 2002). Moreover, similar compounds derived from different N-salicylideneamino acids have been intensively studied and showed some remarkable biological features, from which the antioxidant (Vančo et al., 2008), antiflogistic, antirheumatic (Bauerová et al., 2005), or antidiabetic activities (Vančo et al., 2004) could be considered as the most interesting.

To date, only four X-ray structures of monomeric copper(II) complexes involving the aqua-(N-salicylideneglycinato-κO,N,O')copper(II) moiety in combination with another N-donor ligand, i.e. an alkylated pyridine derivative, have been reported (Warda, 1998a-d). While the present structure is the first one with two-ring one-N-donor aromatic ligand, i.e. 4-methylquinoline (Mqui), there are similarities in the interatomic parameters defining the coordination of the central atom in these complexes.

Two independent formula units of Cu(Salgly)(Mqui)(H₂O).1/2(H₂O) comprise the asymmetric unit of (I), see Fig. 1; each of the solvent water molecules lies on a 2-fold axis. Each Cu^II atom is chelated by two N atoms and a O atom, derived from the Salgly ligand, one N atom from the Mqui ligand. The resultant penta-coordinated geometry is completed by a water molecule. The O atom of the latter ligand occupies an apical position in a slightly distorted square-pyramidal coordination geometry [τ = 0.102 (for Cu1) and 0.091 (for Cu2)]. The bond distances of Cu—N_azomethine [1.927 (3) and 1.926 (3) Å], Cu—N_imine [1.993 (3) and 1.982 (3) Å], Cu—O_carboxy [1.986 (3) and 1.982 (3) Å], Cu—O_phenoxy [1.910 (3) and 1.909 (3) Å] and Cu—O_water [2.371 (3) and 2.367 (3) Å] as well as O_carboxy—Cu—O_phenoxy [166.61 (12) and 166.81 (12) °] and N_azomethine—Cu—N_imine [172.74 (14) and 172.24 (14) °] bond angles are quite similar in the independent complex molecules.

The primary intermolecular contacts in the crystal structure are of the type O—H···O (Fig. 2 & Table 1) and involve both coordinated and free water molecules, and both O atoms of carboxy groups, joining them into linear chains in the [100] direction. Moreover, the secondary structure is stabilized by intermolecular C—H···O interactions and C···C contacts (Fig. 3).

Related literature top

For synthesis, see: Kishita et al. (1964). For related literature, see: Katsuki (2003); Vančo et al. (2004, 2008); Bauerová et al. (2005). For related structures, see: Valent et al. (2002); Warda (1998a,b,c,d).

Experimental top

The title complex, (I), was prepared by the reaction of an ethanol/water solution (2:1, v/v) of aqua-(N-salicylideneglycinato)copper(II) hemihydrate (Kishita et al., 1964) with an ethanolic solution of 4-methylquinoline in the molar ratio of 1:4. The reaction mixture was stirred at 60 °C for 30 minutes. After cooling overnight, well developed single crystals of (I) suitable for X-ray analysis were isolated.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. The molecular structures of the independent complex and water molecules in (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Part of the crystal structure of (I), showing the formation of O—H···O hydrogen bonds as dashed lines [Symmetry codes: (ii) -x + 1, y, -z + 1/2; (iii) -x, y, -z + 1/2].
	Fig. 3. Part of the crystal structure of (I), showing the formation of intermolecular C—H···O interactions (dashed lines) and C···C contacts (dashed lines) with C102···O3ⁱ = 3.6974 (2), C2···C106 = 3.5391 (2), C4···C107 = 3.3636 (2), C4···C108 = 3.3058 (2), C104···C7ⁱ = 3.3946 (2), and C102···C6ⁱ = 3.5122 (2) Å [Symmetry code: (i) x + 1, y, z]. Water molecules of crystallization and H-atoms not involved in hydrogen bonding are omitted for clarity.

Aqua(4-methylquinoline-κN)[N-(2-oxidobenzylidene)glycinato- κ³O,N,O']copper(II) hemihydrate top

Crystal data top

[Cu(C₉H₇NO₃)(C₁₀H₉N)(H₂O)]·0.5H₂O	F(000) = 1696
M_r = 410.9	D_x = 1.533 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 3906 reflections
a = 10.0966 (7) Å	θ = 2.6–26.5°
b = 12.3483 (6) Å	µ = 1.26 mm⁻¹
c = 28.8133 (17) Å	T = 120 K
β = 97.730 (6)°	Prism, blue
V = 3559.7 (4) Å³	0.30 × 0.25 × 0.25 mm
Z = 8

Data collection top

Kuma KM-4-CCD diffractometer	6242 independent reflections
Radiation source: fine-focus sealed tube	4225 reflections with I > 2σ(I)
Enhance (Oxford Diffraction) monochromator	R_int = 0.049
Detector resolution: 8.3611 pixels mm^-1	θ_max = 25.0°, θ_min = 3.2°
rotation method ω scans	h = −12→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −14→13
T_min = 0.690, T_max = 0.729	l = −34→34
19645 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.04P)² + 2.5P] where P = (F_o² + 2F_c²)/3
6242 reflections	(Δ/σ)_max = 0.001
499 parameters	Δρ_max = 0.66 e Å⁻³
6 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[Cu(C₉H₇NO₃)(C₁₀H₉N)(H₂O)]·0.5H₂O	V = 3559.7 (4) Å³
M_r = 410.9	Z = 8
Monoclinic, P2/c	Mo Kα radiation
a = 10.0966 (7) Å	µ = 1.26 mm⁻¹
b = 12.3483 (6) Å	T = 120 K
c = 28.8133 (17) Å	0.30 × 0.25 × 0.25 mm
β = 97.730 (6)°

Data collection top

Kuma KM-4-CCD diffractometer	6242 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	4225 reflections with I > 2σ(I)
T_min = 0.690, T_max = 0.729	R_int = 0.049
19645 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	6 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.66 e Å⁻³
6242 reflections	Δρ_min = −0.54 e Å⁻³
499 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	0.64949 (5)	0.89277 (4)	0.146484 (18)	0.01660 (15)
Cu2	0.14540 (5)	0.52717 (4)	0.145347 (17)	0.01668 (15)
O1	0.4892 (3)	0.8873 (2)	0.17954 (9)	0.0175 (7)
O2	0.3605 (3)	0.7712 (2)	0.21210 (9)	0.0198 (7)
O3	0.7735 (3)	0.8959 (2)	0.10193 (10)	0.0212 (7)
O4	0.7828 (3)	0.8607 (2)	0.21941 (10)	0.0199 (7)
H4V	0.802 (4)	0.7916 (18)	0.2171 (15)	0.030*
H4W	0.733 (4)	0.854 (4)	0.2415 (12)	0.030*
O101	−0.0123 (3)	0.5325 (2)	0.17948 (9)	0.0179 (7)
O102	−0.1400 (3)	0.6477 (2)	0.21334 (9)	0.0208 (7)
O103	0.2671 (3)	0.5247 (2)	0.10008 (10)	0.0221 (7)
O104	0.2815 (3)	0.5589 (2)	0.21757 (10)	0.0195 (7)
H4Y	0.323 (4)	0.621 (2)	0.2148 (15)	0.029*
H4Z	0.231 (4)	0.572 (4)	0.2391 (12)	0.029*
C1	0.4519 (4)	0.7919 (3)	0.18899 (13)	0.0168 (9)
C2	0.5282 (4)	0.6981 (3)	0.17115 (14)	0.0170 (9)
H2A	0.5803	0.6602	0.1979	0.020*
H2B	0.4646	0.6458	0.1543	0.020*
N3	0.6186 (3)	0.7393 (3)	0.13948 (11)	0.0142 (8)
C4	0.6656 (4)	0.6760 (3)	0.11074 (14)	0.0195 (10)
H4	0.6388	0.6022	0.1106	0.023*
C5	0.7556 (4)	0.7073 (3)	0.07865 (13)	0.0179 (9)
C6	0.8021 (4)	0.8155 (4)	0.07522 (14)	0.0214 (10)
C7	0.8874 (4)	0.8365 (4)	0.04121 (15)	0.0248 (10)
H7	0.9184	0.9082	0.0375	0.030*
C8	0.9263 (5)	0.7556 (4)	0.01340 (16)	0.0308 (12)
H8	0.9839	0.7725	−0.0091	0.037*
C9	0.8833 (5)	0.6487 (4)	0.01734 (15)	0.0306 (12)
H9	0.9121	0.5929	−0.0017	0.037*
C10	0.7983 (4)	0.6271 (4)	0.04955 (15)	0.0264 (11)
H10	0.7672	0.5550	0.0522	0.032*
N11	0.6567 (3)	1.0531 (3)	0.15411 (11)	0.0175 (8)
C12	0.7484 (4)	1.0987 (3)	0.18422 (14)	0.0184 (10)
H12	0.8134	1.0533	0.2014	0.022*
C13	0.7568 (4)	1.2106 (4)	0.19281 (15)	0.0237 (10)
H13	0.8264	1.2390	0.2150	0.028*
C14	0.6646 (4)	1.2783 (3)	0.16915 (15)	0.0225 (10)
C15	0.5640 (4)	1.2326 (3)	0.13509 (14)	0.0200 (10)
C16	0.5637 (4)	1.1192 (3)	0.12792 (13)	0.0179 (9)
C17	0.4669 (4)	1.0718 (4)	0.09435 (15)	0.0258 (11)
H17	0.4673	0.9958	0.0892	0.031*
C18	0.3730 (5)	1.1347 (4)	0.06929 (16)	0.0321 (12)
H18	0.3076	1.1023	0.0468	0.039*
C19	0.3712 (5)	1.2475 (4)	0.07621 (17)	0.0336 (12)
H19	0.3054	1.2907	0.0582	0.040*
C20	0.4634 (4)	1.2946 (4)	0.10850 (16)	0.0272 (11)
H20	0.4603	1.3706	0.1133	0.033*
C21	0.6709 (5)	1.3984 (3)	0.17792 (18)	0.0366 (13)
H21A	0.7418	1.4142	0.2037	0.055*
H21B	0.5850	1.4235	0.1862	0.055*
H21C	0.6900	1.4359	0.1496	0.055*
C101	−0.0500 (4)	0.6277 (3)	0.18915 (14)	0.0173 (9)
C102	0.0258 (4)	0.7220 (3)	0.17074 (13)	0.0175 (9)
H10A	−0.0382	0.7751	0.1547	0.021*
H10B	0.0806	0.7591	0.1971	0.021*
N103	0.1120 (3)	0.6801 (3)	0.13791 (11)	0.0159 (8)
C104	0.1625 (4)	0.7452 (3)	0.11094 (13)	0.0174 (9)
H104	0.1374	0.8193	0.1117	0.021*
C105	0.2556 (4)	0.7147 (3)	0.07917 (14)	0.0192 (10)
C106	0.3004 (4)	0.6060 (3)	0.07514 (14)	0.0184 (10)
C107	0.3904 (4)	0.5879 (4)	0.04231 (14)	0.0225 (10)
H107	0.4198	0.5162	0.0375	0.027*
C108	0.4363 (4)	0.6710 (4)	0.01733 (15)	0.0258 (11)
H108	0.4982	0.6555	−0.0039	0.031*
C109	0.3949 (4)	0.7773 (4)	0.02211 (15)	0.0260 (11)
H109	0.4282	0.8343	0.0048	0.031*
C110	0.3047 (4)	0.7971 (4)	0.05253 (14)	0.0233 (10)
H110	0.2743	0.8692	0.0558	0.028*
N111	0.1532 (3)	0.3675 (3)	0.15199 (11)	0.0135 (7)
C112	0.2498 (4)	0.3203 (3)	0.18149 (14)	0.0186 (10)
H112	0.3161	0.3653	0.1982	0.022*
C113	0.2587 (4)	0.2090 (3)	0.18907 (14)	0.0212 (10)
H113	0.3303	0.1805	0.2103	0.025*
C114	0.1658 (5)	0.1406 (4)	0.16633 (15)	0.0227 (10)
C115	0.0611 (4)	0.1873 (3)	0.13443 (14)	0.0201 (10)
C116	0.0567 (4)	0.3009 (3)	0.12845 (14)	0.0184 (10)
C117	−0.0458 (4)	0.3493 (4)	0.09754 (14)	0.0204 (10)
H117	−0.0468	0.4256	0.0932	0.024*
C118	−0.1436 (4)	0.2872 (4)	0.07372 (15)	0.0275 (11)
H118	−0.2133	0.3205	0.0532	0.033*
C119	−0.1422 (5)	0.1741 (4)	0.07931 (15)	0.0272 (11)
H119	−0.2111	0.1313	0.0627	0.033*
C120	−0.0422 (4)	0.1257 (4)	0.10848 (15)	0.0250 (11)
H120	−0.0415	0.0491	0.1115	0.030*
C121	0.1741 (5)	0.0218 (4)	0.17441 (18)	0.0360 (13)
H12A	0.2479	0.0059	0.1992	0.054*
H12B	0.1897	−0.0147	0.1454	0.054*
H12C	0.0900	−0.0040	0.1840	0.054*
O5	0.0000	0.3678 (4)	0.2500	0.0289 (11)
H5V	0.005 (5)	0.412 (3)	0.2745 (11)	0.043*
O6	0.5000	1.0521 (4)	0.2500	0.0267 (10)
H6V	0.486 (5)	1.010 (3)	0.2254 (11)	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0187 (3)	0.0130 (3)	0.0189 (3)	−0.0010 (2)	0.0059 (2)	−0.0003 (2)
Cu2	0.0200 (3)	0.0126 (3)	0.0184 (3)	0.0014 (2)	0.0060 (2)	0.0005 (2)
O1	0.0172 (16)	0.0111 (15)	0.0255 (17)	−0.0003 (12)	0.0073 (13)	−0.0005 (13)
O2	0.0188 (17)	0.0211 (16)	0.0210 (16)	−0.0043 (13)	0.0081 (13)	−0.0015 (13)
O3	0.0272 (18)	0.0169 (16)	0.0217 (16)	−0.0041 (13)	0.0112 (13)	−0.0035 (13)
O4	0.0220 (17)	0.0182 (16)	0.0200 (16)	0.0005 (14)	0.0051 (13)	0.0009 (14)
O101	0.0201 (16)	0.0128 (16)	0.0217 (16)	0.0004 (12)	0.0062 (13)	−0.0003 (12)
O102	0.0224 (17)	0.0204 (16)	0.0214 (16)	0.0026 (13)	0.0099 (13)	0.0018 (13)
O103	0.0284 (18)	0.0158 (16)	0.0248 (17)	0.0030 (13)	0.0136 (14)	0.0027 (13)
O104	0.0240 (18)	0.0180 (16)	0.0177 (16)	−0.0030 (14)	0.0067 (13)	−0.0027 (14)
C1	0.013 (2)	0.021 (2)	0.014 (2)	−0.0017 (19)	−0.0035 (17)	0.0011 (18)
C2	0.016 (2)	0.018 (2)	0.017 (2)	−0.0066 (18)	0.0032 (17)	0.0014 (18)
N3	0.018 (2)	0.0127 (17)	0.0128 (18)	−0.0022 (15)	0.0054 (14)	−0.0002 (15)
C4	0.019 (2)	0.021 (2)	0.017 (2)	0.0015 (19)	−0.0022 (18)	0.0001 (19)
C5	0.017 (2)	0.022 (2)	0.014 (2)	0.0056 (19)	0.0014 (17)	−0.0001 (19)
C6	0.019 (2)	0.027 (3)	0.018 (2)	0.004 (2)	0.0001 (18)	0.000 (2)
C7	0.018 (2)	0.031 (3)	0.027 (3)	0.002 (2)	0.006 (2)	0.002 (2)
C8	0.025 (3)	0.046 (3)	0.022 (3)	0.003 (2)	0.007 (2)	0.002 (2)
C9	0.031 (3)	0.040 (3)	0.021 (2)	0.011 (2)	0.005 (2)	−0.008 (2)
C10	0.025 (3)	0.027 (3)	0.025 (2)	0.005 (2)	−0.003 (2)	−0.002 (2)
N11	0.017 (2)	0.0182 (19)	0.019 (2)	0.0015 (16)	0.0072 (16)	0.0020 (16)
C12	0.021 (2)	0.020 (2)	0.016 (2)	−0.0028 (19)	0.0087 (18)	0.0025 (19)
C13	0.025 (3)	0.023 (3)	0.024 (2)	−0.009 (2)	0.007 (2)	−0.001 (2)
C14	0.029 (3)	0.019 (2)	0.022 (2)	−0.002 (2)	0.014 (2)	0.000 (2)
C15	0.021 (2)	0.021 (2)	0.020 (2)	0.007 (2)	0.0108 (19)	0.0043 (19)
C16	0.022 (2)	0.022 (2)	0.011 (2)	0.0025 (19)	0.0076 (18)	0.0057 (18)
C17	0.024 (3)	0.028 (3)	0.026 (3)	−0.004 (2)	0.004 (2)	0.004 (2)
C18	0.029 (3)	0.043 (3)	0.023 (3)	−0.004 (2)	0.000 (2)	0.009 (2)
C19	0.027 (3)	0.043 (3)	0.032 (3)	0.008 (2)	0.008 (2)	0.019 (3)
C20	0.027 (3)	0.024 (3)	0.034 (3)	0.006 (2)	0.016 (2)	0.009 (2)
C21	0.042 (3)	0.015 (3)	0.054 (4)	0.001 (2)	0.011 (3)	−0.004 (2)
C101	0.020 (2)	0.016 (2)	0.014 (2)	0.0024 (19)	−0.0038 (18)	0.0014 (18)
C102	0.025 (2)	0.014 (2)	0.013 (2)	−0.0009 (19)	0.0046 (18)	−0.0011 (18)
N103	0.0133 (19)	0.0157 (19)	0.0182 (19)	−0.0009 (15)	0.0001 (15)	−0.0004 (16)
C104	0.021 (2)	0.012 (2)	0.018 (2)	0.0010 (18)	−0.0033 (18)	−0.0013 (18)
C105	0.017 (2)	0.022 (2)	0.017 (2)	−0.0003 (19)	−0.0017 (18)	−0.0009 (19)
C106	0.019 (2)	0.023 (2)	0.013 (2)	−0.0007 (19)	0.0009 (18)	−0.0006 (19)
C107	0.023 (3)	0.027 (3)	0.018 (2)	0.003 (2)	0.0040 (19)	−0.004 (2)
C108	0.023 (3)	0.036 (3)	0.020 (2)	−0.004 (2)	0.0061 (19)	−0.001 (2)
C109	0.028 (3)	0.030 (3)	0.021 (2)	−0.009 (2)	0.004 (2)	0.007 (2)
C110	0.030 (3)	0.019 (2)	0.021 (2)	−0.003 (2)	0.002 (2)	0.0013 (19)
N111	0.0168 (19)	0.0130 (17)	0.0121 (17)	0.0010 (15)	0.0074 (14)	−0.0007 (15)
C112	0.015 (2)	0.020 (2)	0.022 (2)	0.0020 (19)	0.0039 (18)	0.0002 (19)
C113	0.030 (3)	0.022 (2)	0.012 (2)	0.005 (2)	0.0030 (18)	0.0027 (19)
C114	0.031 (3)	0.017 (2)	0.021 (2)	0.002 (2)	0.010 (2)	0.002 (2)
C115	0.028 (3)	0.015 (2)	0.020 (2)	0.0014 (19)	0.0118 (19)	−0.0003 (19)
C116	0.018 (2)	0.017 (2)	0.022 (2)	−0.0004 (19)	0.0114 (18)	−0.0010 (19)
C117	0.024 (3)	0.021 (2)	0.017 (2)	0.002 (2)	0.0061 (19)	−0.0029 (19)
C118	0.020 (3)	0.039 (3)	0.024 (3)	−0.002 (2)	0.002 (2)	−0.001 (2)
C119	0.026 (3)	0.033 (3)	0.026 (3)	−0.011 (2)	0.013 (2)	−0.012 (2)
C120	0.032 (3)	0.019 (2)	0.027 (3)	−0.008 (2)	0.011 (2)	−0.007 (2)
C121	0.049 (3)	0.021 (3)	0.038 (3)	−0.001 (2)	0.006 (3)	0.002 (2)
O5	0.043 (3)	0.022 (2)	0.023 (3)	0.000	0.008 (2)	0.000
O6	0.040 (3)	0.024 (3)	0.017 (2)	0.000	0.005 (2)	0.000

Geometric parameters (Å, º) top

Cu1—O3	1.910 (3)	C17—H17	0.9500
Cu1—N3	1.927 (3)	C18—C19	1.408 (7)
Cu1—O1	1.986 (3)	C18—H18	0.9500
Cu1—N11	1.993 (3)	C19—C20	1.355 (7)
Cu1—O4	2.371 (3)	C19—H19	0.9500
Cu2—O103	1.909 (3)	C20—H20	0.9500
Cu2—N103	1.926 (3)	C21—H21A	0.9800
Cu2—N111	1.982 (3)	C21—H21B	0.9800
Cu2—O101	1.982 (3)	C21—H21C	0.9800
Cu2—O104	2.367 (3)	C101—C102	1.527 (5)
O1—C1	1.276 (5)	C102—N103	1.463 (5)
O2—C1	1.235 (5)	C102—H10A	0.9900
O3—C6	1.312 (5)	C102—H10B	0.9900
O4—H4V	0.879 (19)	N103—C104	1.272 (5)
O4—H4W	0.87 (4)	C104—C105	1.447 (6)
O101—C101	1.278 (5)	C104—H104	0.9500
O102—C101	1.242 (5)	C105—C110	1.405 (6)
O103—C106	1.305 (5)	C105—C106	1.426 (6)
O104—H4Y	0.879 (19)	C106—C107	1.415 (6)
O104—H4Z	0.87 (4)	C107—C108	1.369 (6)
C1—C2	1.518 (6)	C107—H107	0.9500
C2—N3	1.465 (5)	C108—C109	1.390 (6)
C2—H2A	0.9900	C108—H108	0.9500
C2—H2B	0.9900	C109—C110	1.368 (6)
N3—C4	1.276 (5)	C109—H109	0.9500
C4—C5	1.434 (5)	C110—H110	0.9500
C4—H4	0.9500	N111—C112	1.338 (5)
C5—C10	1.403 (6)	N111—C116	1.381 (5)
C5—C6	1.424 (6)	C112—C113	1.392 (6)
C6—C7	1.413 (6)	C112—H112	0.9500
C7—C8	1.371 (6)	C113—C114	1.363 (6)
C7—H7	0.9500	C113—H113	0.9500
C8—C9	1.398 (6)	C114—C115	1.426 (6)
C8—H8	0.9500	C114—C121	1.486 (6)
C9—C10	1.373 (6)	C115—C116	1.414 (6)
C9—H9	0.9500	C115—C120	1.419 (6)
C10—H10	0.9500	C116—C117	1.404 (6)
N11—C12	1.308 (5)	C117—C118	1.361 (6)
N11—C16	1.388 (5)	C117—H117	0.9500
C12—C13	1.404 (6)	C118—C119	1.406 (6)
C12—H12	0.9500	C118—H118	0.9500
C13—C14	1.364 (6)	C119—C120	1.362 (6)
C13—H13	0.9500	C119—H119	0.9500
C14—C15	1.430 (6)	C120—H120	0.9500
C14—C21	1.505 (6)	C121—H12A	0.9800
C15—C20	1.413 (6)	C121—H12B	0.9800
C15—C16	1.416 (6)	C121—H12C	0.9800
C16—C17	1.407 (6)	O5—H5V	0.890 (19)
C17—C18	1.357 (6)	O6—H6V	0.876 (19)

O3—Cu1—N3	93.49 (12)	C17—C18—C19	120.8 (4)
O3—Cu1—O1	166.61 (12)	C17—C18—H18	119.6
N3—Cu1—O1	83.42 (12)	C19—C18—H18	119.6
O3—Cu1—N11	92.10 (12)	C20—C19—C18	120.1 (4)
N3—Cu1—N11	172.74 (14)	C20—C19—H19	120.0
O1—Cu1—N11	90.08 (12)	C18—C19—H19	120.0
O3—Cu1—O4	104.68 (11)	C19—C20—C15	121.2 (4)
N3—Cu1—O4	89.61 (12)	C19—C20—H20	119.4
O1—Cu1—O4	88.37 (11)	C15—C20—H20	119.4
N11—Cu1—O4	93.45 (12)	C14—C21—H21A	109.5
O103—Cu2—N103	93.38 (13)	C14—C21—H21B	109.5
O103—Cu2—N111	91.68 (12)	H21A—C21—H21B	109.5
N103—Cu2—N111	172.24 (14)	C14—C21—H21C	109.5
O103—Cu2—O101	166.81 (12)	H21A—C21—H21C	109.5
N103—Cu2—O101	83.24 (12)	H21B—C21—H21C	109.5
N111—Cu2—O101	90.51 (12)	O102—C101—O101	124.6 (4)
O103—Cu2—O104	104.63 (11)	O102—C101—C102	118.8 (4)
N103—Cu2—O104	90.45 (12)	O101—C101—C102	116.6 (4)
N111—Cu2—O104	93.96 (12)	N103—C102—C101	108.9 (3)
O101—Cu2—O104	88.19 (11)	N103—C102—H10A	109.9
C1—O1—Cu1	114.6 (3)	C101—C102—H10A	109.9
C6—O3—Cu1	126.5 (3)	N103—C102—H10B	109.9
Cu1—O4—H4V	101 (3)	C101—C102—H10B	109.9
Cu1—O4—H4W	110 (3)	H10A—C102—H10B	108.3
H4V—O4—H4W	96 (4)	C104—N103—C102	119.6 (3)
C101—O101—Cu2	114.9 (3)	C104—N103—Cu2	127.5 (3)
C106—O103—Cu2	126.9 (3)	C102—N103—Cu2	112.7 (2)
Cu2—O104—H4Y	107 (3)	N103—C104—C105	124.8 (4)
Cu2—O104—H4Z	110 (3)	N103—C104—H104	117.6
H4Y—O104—H4Z	103 (4)	C105—C104—H104	117.6
O2—C1—O1	124.7 (4)	C110—C105—C106	119.9 (4)
O2—C1—C2	118.3 (4)	C110—C105—C104	117.7 (4)
O1—C1—C2	117.0 (3)	C106—C105—C104	122.4 (4)
N3—C2—C1	109.4 (3)	O103—C106—C107	118.8 (4)
N3—C2—H2A	109.8	O103—C106—C105	124.9 (4)
C1—C2—H2A	109.8	C107—C106—C105	116.3 (4)
N3—C2—H2B	109.8	C108—C107—C106	121.7 (4)
C1—C2—H2B	109.8	C108—C107—H107	119.1
H2A—C2—H2B	108.2	C106—C107—H107	119.1
C4—N3—C2	120.6 (3)	C107—C108—C109	121.9 (4)
C4—N3—Cu1	126.9 (3)	C107—C108—H108	119.1
C2—N3—Cu1	112.4 (2)	C109—C108—H108	119.1
N3—C4—C5	125.2 (4)	C110—C109—C108	117.9 (4)
N3—C4—H4	117.4	C110—C109—H109	121.1
C5—C4—H4	117.4	C108—C109—H109	121.1
C10—C5—C6	119.4 (4)	C109—C110—C105	122.3 (4)
C10—C5—C4	117.9 (4)	C109—C110—H110	118.8
C6—C5—C4	122.8 (4)	C105—C110—H110	118.8
O3—C6—C7	118.1 (4)	C112—N111—C116	117.3 (3)
O3—C6—C5	124.6 (4)	C112—N111—Cu2	120.7 (3)
C7—C6—C5	117.3 (4)	C116—N111—Cu2	121.9 (3)
C8—C7—C6	121.4 (4)	N111—C112—C113	123.7 (4)
C8—C7—H7	119.3	N111—C112—H112	118.1
C6—C7—H7	119.3	C113—C112—H112	118.1
C7—C8—C9	121.6 (4)	C114—C113—C112	120.7 (4)
C7—C8—H8	119.2	C114—C113—H113	119.6
C9—C8—H8	119.2	C112—C113—H113	119.6
C10—C9—C8	117.9 (4)	C113—C114—C115	117.5 (4)
C10—C9—H9	121.1	C113—C114—C121	121.1 (4)
C8—C9—H9	121.1	C115—C114—C121	121.4 (4)
C9—C10—C5	122.5 (4)	C116—C115—C120	117.3 (4)
C9—C10—H10	118.8	C116—C115—C114	119.2 (4)
C5—C10—H10	118.8	C120—C115—C114	123.5 (4)
C12—N11—C16	118.3 (4)	N111—C116—C117	118.0 (4)
C12—N11—Cu1	120.9 (3)	N111—C116—C115	121.5 (4)
C16—N11—Cu1	120.8 (3)	C117—C116—C115	120.5 (4)
N11—C12—C13	124.1 (4)	C118—C117—C116	120.2 (4)
N11—C12—H12	117.9	C118—C117—H117	119.9
C13—C12—H12	117.9	C116—C117—H117	119.9
C14—C13—C12	119.6 (4)	C117—C118—C119	120.4 (4)
C14—C13—H13	120.2	C117—C118—H118	119.8
C12—C13—H13	120.2	C119—C118—H118	119.8
C13—C14—C15	118.4 (4)	C120—C119—C118	120.1 (4)
C13—C14—C21	120.6 (4)	C120—C119—H119	119.9
C15—C14—C21	121.0 (4)	C118—C119—H119	119.9
C20—C15—C16	118.0 (4)	C119—C120—C115	121.4 (4)
C20—C15—C14	123.4 (4)	C119—C120—H120	119.3
C16—C15—C14	118.6 (4)	C115—C120—H120	119.3
N11—C16—C17	119.1 (4)	C114—C121—H12A	109.5
N11—C16—C15	120.9 (4)	C114—C121—H12B	109.5
C17—C16—C15	120.0 (4)	H12A—C121—H12B	109.5
C18—C17—C16	119.9 (4)	C114—C121—H12C	109.5
C18—C17—H17	120.0	H12A—C121—H12C	109.5
C16—C17—H17	120.0	H12B—C121—H12C	109.5

O3—Cu1—O1—C1	88.7 (5)	C14—C15—C16—C17	−179.4 (4)
N3—Cu1—O1—C1	11.4 (3)	N11—C16—C17—C18	178.3 (4)
N11—Cu1—O1—C1	−171.9 (3)	C15—C16—C17—C18	−0.8 (6)
O4—Cu1—O1—C1	−78.4 (3)	C16—C17—C18—C19	0.3 (7)
N3—Cu1—O3—C6	6.8 (3)	C17—C18—C19—C20	−0.6 (7)
O1—Cu1—O3—C6	−69.4 (6)	C18—C19—C20—C15	1.2 (7)
N11—Cu1—O3—C6	−168.6 (3)	C16—C15—C20—C19	−1.7 (6)
O4—Cu1—O3—C6	97.3 (3)	C14—C15—C20—C19	179.2 (4)
O103—Cu2—O101—C101	−87.7 (6)	Cu2—O101—C101—O102	−174.3 (3)
N103—Cu2—O101—C101	−11.9 (3)	Cu2—O101—C101—C102	3.4 (4)
N111—Cu2—O101—C101	172.8 (3)	O102—C101—C102—N103	−171.8 (3)
O104—Cu2—O101—C101	78.8 (3)	O101—C101—C102—N103	10.4 (5)
N103—Cu2—O103—C106	−1.9 (3)	C101—C102—N103—C104	165.2 (3)
N111—Cu2—O103—C106	172.3 (3)	C101—C102—N103—Cu2	−19.5 (4)
O101—Cu2—O103—C106	72.8 (6)	O103—Cu2—N103—C104	−0.5 (4)
O104—Cu2—O103—C106	−93.2 (3)	O101—Cu2—N103—C104	−167.7 (4)
Cu1—O1—C1—O2	174.8 (3)	O104—Cu2—N103—C104	104.2 (3)
Cu1—O1—C1—C2	−3.8 (4)	O103—Cu2—N103—C102	−175.4 (3)
O2—C1—C2—N3	172.2 (3)	O101—Cu2—N103—C102	17.4 (3)
O1—C1—C2—N3	−9.0 (5)	O104—Cu2—N103—C102	−70.7 (3)
C1—C2—N3—C4	−161.0 (4)	C102—N103—C104—C105	176.0 (4)
C1—C2—N3—Cu1	17.7 (4)	Cu2—N103—C104—C105	1.3 (6)
O3—Cu1—N3—C4	−4.4 (4)	N103—C104—C105—C110	−178.5 (4)
O1—Cu1—N3—C4	162.6 (4)	N103—C104—C105—C106	−0.1 (6)
O4—Cu1—N3—C4	−109.0 (3)	Cu2—O103—C106—C107	−178.5 (3)
O3—Cu1—N3—C2	177.0 (3)	Cu2—O103—C106—C105	3.4 (6)
O1—Cu1—N3—C2	−16.0 (3)	C110—C105—C106—O103	175.9 (4)
O4—Cu1—N3—C2	72.4 (3)	C104—C105—C106—O103	−2.4 (6)
C2—N3—C4—C5	−179.3 (4)	C110—C105—C106—C107	−2.2 (6)
Cu1—N3—C4—C5	2.2 (6)	C104—C105—C106—C107	179.4 (4)
N3—C4—C5—C10	179.6 (4)	O103—C106—C107—C108	−175.5 (4)
N3—C4—C5—C6	−0.6 (6)	C105—C106—C107—C108	2.7 (6)
Cu1—O3—C6—C7	174.1 (3)	C106—C107—C108—C109	−1.4 (7)
Cu1—O3—C6—C5	−7.3 (6)	C107—C108—C109—C110	−0.6 (7)
C10—C5—C6—O3	−176.9 (4)	C108—C109—C110—C105	1.1 (7)
C4—C5—C6—O3	3.3 (6)	C106—C105—C110—C109	0.4 (6)
C10—C5—C6—C7	1.6 (6)	C104—C105—C110—C109	178.8 (4)
C4—C5—C6—C7	−178.1 (4)	O103—Cu2—N111—C112	85.4 (3)
O3—C6—C7—C8	177.2 (4)	O101—Cu2—N111—C112	−107.6 (3)
C5—C6—C7—C8	−1.5 (6)	O104—Cu2—N111—C112	−19.4 (3)
C6—C7—C8—C9	0.1 (7)	O103—Cu2—N111—C116	−97.9 (3)
C7—C8—C9—C10	1.2 (7)	O101—Cu2—N111—C116	69.1 (3)
C8—C9—C10—C5	−1.0 (7)	O104—Cu2—N111—C116	157.4 (3)
C6—C5—C10—C9	−0.4 (6)	C116—N111—C112—C113	0.8 (6)
C4—C5—C10—C9	179.3 (4)	Cu2—N111—C112—C113	177.7 (3)
O3—Cu1—N11—C12	−86.6 (3)	N111—C112—C113—C114	−0.5 (6)
O1—Cu1—N11—C12	106.6 (3)	C112—C113—C114—C115	0.6 (6)
O4—Cu1—N11—C12	18.3 (3)	C112—C113—C114—C121	−179.6 (4)
O3—Cu1—N11—C16	94.1 (3)	C113—C114—C115—C116	−1.1 (6)
O1—Cu1—N11—C16	−72.7 (3)	C121—C114—C115—C116	179.2 (4)
O4—Cu1—N11—C16	−161.1 (3)	C113—C114—C115—C120	−179.9 (4)
C16—N11—C12—C13	1.8 (6)	C121—C114—C115—C120	0.3 (7)
Cu1—N11—C12—C13	−177.5 (3)	C112—N111—C116—C117	179.7 (4)
N11—C12—C13—C14	0.6 (6)	Cu2—N111—C116—C117	2.8 (5)
C12—C13—C14—C15	−1.9 (6)	C112—N111—C116—C115	−1.3 (6)
C12—C13—C14—C21	179.6 (4)	Cu2—N111—C116—C115	−178.2 (3)
C13—C14—C15—C20	180.0 (4)	C120—C115—C116—N111	−179.6 (4)
C21—C14—C15—C20	−1.5 (6)	C114—C115—C116—N111	1.5 (6)
C13—C14—C15—C16	0.8 (6)	C120—C115—C116—C117	−0.6 (6)
C21—C14—C15—C16	179.3 (4)	C114—C115—C116—C117	−179.6 (4)
C12—N11—C16—C17	178.1 (4)	N111—C116—C117—C118	−179.6 (4)
Cu1—N11—C16—C17	−2.6 (5)	C115—C116—C117—C118	1.4 (6)
C12—N11—C16—C15	−2.9 (6)	C116—C117—C118—C119	−0.9 (6)
Cu1—N11—C16—C15	176.5 (3)	C117—C118—C119—C120	−0.4 (6)
C20—C15—C16—N11	−177.6 (4)	C118—C119—C120—C115	1.1 (6)
C14—C15—C16—N11	1.6 (6)	C116—C115—C120—C119	−0.6 (6)
C20—C15—C16—C17	1.4 (6)	C114—C115—C120—C119	178.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4V···O102ⁱ	0.88 (2)	1.88 (2)	2.756 (4)	174 (4)
O4—H4W···O2ⁱⁱ	0.87 (4)	2.01 (3)	2.825 (4)	155 (4)
O5—H5V···O101ⁱⁱⁱ	0.89 (2)	1.99 (2)	2.865 (4)	169 (4)
O6—H6V···O1	0.88 (2)	2.01 (2)	2.867 (4)	165 (4)
O104—H4Y···O2	0.88 (2)	1.90 (2)	2.751 (4)	162 (4)
O104—H4Z···O102ⁱⁱⁱ	0.87 (4)	1.98 (2)	2.823 (4)	162 (4)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₉H₇NO₃)(C₁₀H₉N)(H₂O)]·0.5H₂O
M_r	410.9
Crystal system, space group	Monoclinic, P2/c
Temperature (K)	120
a, b, c (Å)	10.0966 (7), 12.3483 (6), 28.8133 (17)
β (°)	97.730 (6)
V (Å³)	3559.7 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.26
Crystal size (mm)	0.30 × 0.25 × 0.25

Data collection
Diffractometer	Kuma KM-4-CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.690, 0.729
No. of measured, independent and observed [I > 2σ(I)] reflections	19645, 6242, 4225
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.113, 1.09
No. of reflections	6242
No. of parameters	499
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.54

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4V···O102ⁱ	0.879 (19)	1.88 (2)	2.756 (4)	174 (4)
O4—H4W···O2ⁱⁱ	0.87 (4)	2.01 (3)	2.825 (4)	155 (4)
O5—H5V···O101ⁱⁱⁱ	0.890 (19)	1.99 (2)	2.865 (4)	169 (4)
O6—H6V···O1	0.876 (19)	2.01 (2)	2.867 (4)	165 (4)
O104—H4Y···O2	0.879 (19)	1.90 (2)	2.751 (4)	162 (4)
O104—H4Z···O102ⁱⁱⁱ	0.87 (4)	1.98 (2)	2.823 (4)	162 (4)

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

Acknowledgements

Financial support of this work by the Ministry of Education, Youth and Sports of the Czech Republic (grant Nos. MSM6198959218, MSM0021622415 and MSM6215712403) and the Scientific Grant Agency of the Ministry of Education of the Slovak Republic (grant No. VEGA 1/3416/06) is gratefully acknowledged.

References

Bauerová, K., Valentová, J., Poništ, S., Navarová, J., Komendová, D. & Mihalová, D. (2005). Biologia, 60, 65–68. Google Scholar
Brandenburg, K. (2006). DIAMOND. Release 3.1e. Crystal Impact GbR, Bonn, Germany. Google Scholar
Katsuki, T. (2003). Synlett, pp. 281–297. Web of Science CrossRef Google Scholar
Kishita, M., Nakahara, A. & Kubo, M. (1964). Aust. J. Chem. 17, 810–816. CrossRef CAS Google Scholar
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Versions 1.171.31.7. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany. Google Scholar
Valent, A., Melník, M., Hudecová, D., Dudová, B., Kivekäs, R. & Sundberg, M. R. (2002). Inorg. Chim. Acta, 340, 15–20. Web of Science CSD CrossRef CAS Google Scholar
Vančo, J., Marek, J., Trávníček, Z., Račanská, E., Muselík, J. & Švajlenová, O. (2008). J. Inorg. Biochem. In the press. doi:10.1016/j.jinorgbio.2007.10.003. Google Scholar
Vančo, J., Švajlenová, O., Račanská, E., Muselík, J. & Valentová, J. (2004). J. Trace Elem. Med. Biol. 18, 155–161. Web of Science PubMed Google Scholar
Warda, S. A. (1998a). Acta Cryst. C54, 187–189. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Warda, S. A. (1998b). Acta Cryst. C54, 768–770. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Warda, S. A. (1998c). Acta Cryst. C54, 1236–1238. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Warda, S. A. (1998d). Acta Cryst. C54, 1754–1755. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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