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In the title compound, {[Cu(C7H8N5O4)Cl(H2O)]·H2O}n, the bond lengths in the N-pyrimidinylglycinate unit provide evidence for a strongly polarized electronic structure. This ligand is coordinated to three CuII centres, resulting in the formation of a coordination polymer in the form of a chain containing two types of centrosymmetric ring. These chains are linked by an extensive series of hydrogen bonds, including O-H...O, N-H...O, O-H...Cl and N-H...Cl types, into a continuous three-dimensional structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109018149/sk3322sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270109018149/sk3322Isup2.hkl
Contains datablock I

CCDC reference: 742166

Comment top

The structure of the title compound (I) was reported some years ago, determined using diffraction data collected at ambient temperature (Moreno et al., 1999). This determination was reported essentially on a proof of constitution basis, with no discussion either of the geometry of the organic ligand or of the hydrogen bonding: indeed, the non-coordinated water component was not mentioned anywhere in this report. Since the publication of this mixed-ligand structure, the geometries of amino-acid-substituted pyrimidinones of the type present in compound (I) have been extensively analysed (Low et al., 2000; Low, Moreno Sánchez et al., 2001), as these systems consistently exhibit some highly unusual geometric features. Similarly, since the report of Moreno et al. (1999), the structures have been reported for a substantial number of complexes and salts formed by the same organic ligand with a variety of metal ions, and these encompass a very wide range of architectures. Accordingly, we have now taken the opportunity to redetermine the structure of (I) (Fig. 1) using diffraction data collected at 120 K, and here we (a) discuss the geometry of the organic ligand in (I); (b) re-evaluate the copper geometry and compare the coordination polymer formed in (I) with those formed by the same organic ligand with a wide variety of other metal ions; and (c) discuss the hydrogen-bonding system which links the coordination polymer chains in (I).

The bond distances within the pyrimidinylglycinate unit (Table 1) show a number of unusual values. The distances C4—C5 and C5—C6, which represent formally single and double bonds, respectively, differ only slightly; the four C—N distances between N2 and N6 span only a narrow range, and the shortest of these distances corresponds to the formal single bond C6—N6 rather than to the formal double bond N1—C2; and the distances C5—N5 and N5—O5 differ by only ca 0.08 Å, whereas in simple unperturbed C-nitroso compounds, this difference generally exceeds 0.20 Å (Talberg, 1977; Schlemper et al., 1986). Taken together, these observations indicate that the polarized, charge-separated form (B) (see Scheme) is a more appropriate representation of the electronic structure than the classically localized form (A).

The Cu centre in the title compound (I) shows the usual (4 + 2) distorted octahedral coordination, augmented by a rather long contact to the nitroso atom O5 (Table 1), which itself may be associated with the polarized electronic structure which leads to an enhanced negative charge at atom O5. This contact could be interpreted as one component of a very asymmetric η2 coordination of the nitroso group; such coordination contrasts with the corresponding coordination in the potassium complex [K(L)(H2O)] (Low, Moreno Sánchez et al., 2001) where the K—N and K—O distances are 3.016 (2) and 3.132 (2) Å, respectively, indicating almost ideally symmetric η2 coordination. The coordination polyhedron of the Cu at (x, y, z) consists of a chloride ion and a water molecule, the atoms O4, N5 and O5 from the pyrimidinylglycinate anion at (x, y, z) and the carboxylate atoms O21 and O22 from the pyrimidinylglycinate anions at (x, y, 1 + z) and (1 - x, 1 - y, 1 - z), respectively. The axial sites in the elongated pseudo-octahedron are occupied by the ketonic atom O4 and the carboxylate atom O21 at (x, y, 1 + z). However, it seems unwise to invoke the Jahn–Teller effect as an explanation of the geometry at the Cu centre. With such a disparate group of ligating atoms, even ignoring the long contact to the nitroso O atom but including both neutral and anionic O atoms as well as three anionic ligands in a mer arrangement, it is implausible that any selection of metal ligand distances could give rise to a degenerate electronic configuration at Cu.

The pyrimidinylglycinate anion at (x, y, z) thus coordinates to three Cu atoms, those at (x, y, z), (x, y, -1 + z) and (1 - x, 1 - y, 1 - z). Propagation by translation and inversion of these ligating interactions generates a one-dimensional coordination polymer in the form of a chain of centrosymmetric edge-fused rings running parallel to the [001] direction, in which eight-membered rings centred at (1/2, 1/2, n), where n represents an integer, alternate with 18-membered rings centred at (1/2, 1/2, 0.5 + n), where n represents an integer (Fig. 2).

This chain of edge-fused rings appears to be a unique motif in metal complexes of the ligand (L)-. One-dimensional coordination polymers containing the ligand (L)- have previously been reported for the isostructural pair of complexes [M(L)2(H2O)5].H2O based on strontium (Glidewell et al., 2002) and barium (Godino Salido et al., 2004), where the metal centres are eight coordinate, and where the polymer takes the form of a simple chain with no ring formation. By contrast, the calcium complex [Ca(L)2(H2O)4].4(H2O) contains finite aggregates in which the Ca is six coordinate (Godino Salido et al., 2004); the manganese complex [Mn(L)2((H2O)4)].6(H2O) similarly forms a finite aggregate (Low, Moreno Sánchez et al., 2001). Two-dimensional coordination polymers in the form of organic–inorganic hybrid sheets are formed in both the sodium and potassium derivatives, [Na2(L)2(H2O)3] and [K(L)(H2O)], in which the metal ions are, respectively, five and seven coordinate, including an unusual η2 coordination of the nitroso group in (L)- to potassium (Low, Moreno Sánchez et al., 2001). The lithium compound [Li(L)(H2O)3], on the other hand, forms a finite complex containing tetrahedral Li (Low, Moreno Sánchez et al., 2001). Different from all of these complexes in which the anion (L)- acts as a coordinating ligand, are the magnesium (Arranz Mascarós et al., 2000) and the zinc complexes (Arranz-Mascarós et al., 1999), [M(H2O)6](L-)2.2(H2O), which despite having identical constitutions are not isomorphous: here the anion is not coordinated to the metal centre, but forms simple salts with the hexa-aqua cations. However, chains of spiro-fused rings are formed in the calcium (Low, Arranz et al., 2001) and strontium (Godino Salido et al., 2004) complexes of the analogous pyrimidinylglycylglycinate anion (L')- (see Scheme). These Ca and Sr complexes crystallize as a trihydrate and as a tetrahydrate, respectively, but they are effectively isomorphous and almost isostructural, with the metal centres lying on twofold rotation axes in space group C2/c.

An extensive series of hydrogen bonds encompassing O—H···O, N—H···O, O—H···Cl and N—H···Cl types (Table 2) links the coordination polymer chains into a continuous three-dimensional framework of considerable complexity. However, the formation of this framework is readily analysed in terms of just the two N—H···Cl hydrogen bonds, which generate a sheet lying parallel to (001) (Fig. 3). The combination of this simple sheet and the chains along [001] is sufficient to generate the three-dimensional structure. The framework is considerably strengthened by the hydrogen bonds formed by the water molecules: the coordinated water molecule acts as a double donor of hydrogen bonds, while the non-coordinated water molecule acts as both a double donor and a double acceptor of hydrogen bonds.

Regardless of whether simple salts are formed as for Mg and Zn, or finite aggregates as for Li and Ca, or one-dimensional coordination polymers as for Sr and Ba, or two-dimensional coordination polymers as for Na and K, extensive hydrogen bonding links the metal-containing components, the non-coordinated water molecules where these are present and the free anions where these are present into a continuous three-dimensional framework structure in every case. Thus, in all metal derivatives containing the anion (L)-, either as a ligand or as a counterion, which have so far been structurally characterized the components are linked by hydrogen bonds into three-dimensional systems, regardless of the overall composition of the material and of the nature of the interactions between the metal ion and (L)-.

Related literature top

For related literature, see: Arranz Mascarós et al. (2000); Arranz-Mascarós et al. (1999); Glidewell et al. (2002); Godino Salido et al. (2004); Low et al. (2000); Low, Arranz et al. (2001); Low, Moreno Sánchez et al. (2001); Moreno et al. (1999); Schlemper et al. (1986); Talberg (1977).

Experimental top

The compound was prepared by the published method (Moreno et al., 1999).

Refinement top

All H atoms were located in difference maps. H atoms bonded to C atoms were then treated as riding atoms in geometrically idealized positions with C—H distances 0.98 Å (CH3) or 0.99 Å (CH2) and with Uiso(H) = kUeq(C), where k = 1.5 for the methyl group which was permitted to rotate but not to tilt and 1.2 for the other H atoms bonded to C atoms. The H atoms bonded to N atoms were initially treated as riding atoms in geometrically idealized positions with N—H distances of 0.88 Å and Uiso(H) = kUeq(N), while the H atoms of the two water molecules were initially permitted to ride at the distances deduced from the difference maps with Uiso(H) = 1.2Ueq(O). In the final refinement cycles the coordinates of the H atoms bonded to N and O atoms were freely refined giving N—H distances in the range 0.81 (3)–0.85 (3) Å, O—H distances in the range 0.77 (3)–0.83 (4) Å, and H—O—H angles of 110 (3)° and 113 (3)°. None of the residual features in the difference map could plausibly be reconciled with any further chemical entities, but they possibly reflect the relatively poorer quality of the weak data, particularly those beyond (sin θ)/λ = 0.60.

Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of compound (I) showing the atom-labelling scheme and the coordination of the Cu centre, but with the long contact to O5 omitted. Displacement ellipsoids are shown at the 30% probability level and the atoms marked with 'b' or 'c' are at the symmetry positions (x, y, 1 + z) and (1 - x, 1 - y, 1 - z), respectively.
[Figure 2] Fig. 2. A stereoview of part of the crystal structure of compound (I) showing the formation of a coordination polymer chain parallel to the [001] direction. For the sake of clarity, the non-coordinated water molecule and all of the H atoms have been omitted, as has the long contact between atoms Cu1 and O5.
[Figure 3] Fig. 3. A stereoview of part of the crystal structure of compound (I) showing the formation of a hydrogen-bonded sheet parallel to (001). For the sake of clarity, the non-coordinated water molecule and the H atoms bonded to C or O atoms have been omitted, as has the long contact between atoms Cu1 and O5.
catena-Poly[[[aquachloridocopper(II)]-µ-N-(6-amino-3-methyl- 5-nitroso-4-oxo-3,4-dihydropyrimidin-2-yl)glycinato] monohydrate] top
Crystal data top
[Cu(C7H8N5O4)Cl(H2O)]·H2OZ = 2
Mr = 361.21F(000) = 366
Triclinic, P1Dx = 1.906 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9807 (5) ÅCell parameters from 2889 reflections
b = 9.1462 (6) Åθ = 2.0–27.5°
c = 11.2512 (6) ŵ = 1.98 mm1
α = 107.357 (5)°T = 120 K
β = 105.037 (5)°Block, blue
γ = 102.028 (6)°0.41 × 0.25 × 0.22 mm
V = 629.54 (8) Å3
Data collection top
Bruker Nonius KappaCCD
diffractometer
2889 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode2569 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.084
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.0°
ϕ & ω scansh = 19
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1111
Tmin = 0.601, Tmax = 0.647l = 1414
3745 measured reflections
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0331P)2 + 0.367P]
where P = (Fo2 + 2Fc2)/3
2889 reflections(Δ/σ)max = 0.001
203 parametersΔρmax = 0.72 e Å3
0 restraintsΔρmin = 0.66 e Å3
Crystal data top
[Cu(C7H8N5O4)Cl(H2O)]·H2Oγ = 102.028 (6)°
Mr = 361.21V = 629.54 (8) Å3
Triclinic, P1Z = 2
a = 6.9807 (5) ÅMo Kα radiation
b = 9.1462 (6) ŵ = 1.98 mm1
c = 11.2512 (6) ÅT = 120 K
α = 107.357 (5)°0.41 × 0.25 × 0.22 mm
β = 105.037 (5)°
Data collection top
Bruker Nonius KappaCCD
diffractometer
2889 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2569 reflections with I > 2σ(I)
Tmin = 0.601, Tmax = 0.647Rint = 0.084
3745 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.72 e Å3
2889 reflectionsΔρmin = 0.66 e Å3
203 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.29780 (4)0.33211 (3)0.76823 (2)0.02311 (9)
Cl10.08612 (9)0.07568 (6)0.70490 (5)0.02917 (13)
N10.4639 (3)0.1791 (2)0.32186 (17)0.0245 (4)
C20.2967 (3)0.2220 (2)0.28061 (19)0.0202 (4)
N30.1962 (3)0.2928 (2)0.36055 (17)0.0223 (3)
C40.2510 (3)0.3052 (2)0.49225 (19)0.0207 (4)
C50.4289 (3)0.2522 (2)0.53803 (19)0.0208 (4)
C60.5348 (3)0.1931 (2)0.4488 (2)0.0214 (4)
N20.2179 (3)0.1932 (2)0.15159 (17)0.0238 (4)
H20.108 (4)0.210 (3)0.122 (3)0.029*
C210.3400 (4)0.1653 (2)0.0656 (2)0.0251 (4)
H21A0.24460.10520.02720.030*
H21B0.42540.09800.09010.030*
C220.4830 (3)0.3219 (2)0.0746 (2)0.0233 (4)
O210.5637 (3)0.3138 (2)0.01310 (17)0.0375 (4)
O220.5063 (3)0.44739 (19)0.16947 (16)0.0308 (3)
C30.0182 (4)0.3450 (4)0.3077 (2)0.0395 (6)
H3A0.05750.41580.26170.059*
H3B0.02180.40360.38080.059*
H3C0.09980.25040.24520.059*
O40.1545 (3)0.3587 (2)0.56229 (15)0.0294 (3)
N50.4750 (3)0.2599 (2)0.66369 (17)0.0233 (3)
O50.6289 (3)0.2209 (2)0.71611 (16)0.0372 (4)
N60.6983 (3)0.1474 (3)0.4873 (2)0.0301 (4)
H6A0.746 (5)0.109 (4)0.427 (3)0.036*
H6B0.739 (5)0.160 (3)0.565 (3)0.036*
O310.1322 (3)0.4182 (2)0.87222 (19)0.0339 (4)
H3110.059 (5)0.358 (4)0.894 (3)0.041*
H3120.214 (5)0.491 (4)0.932 (3)0.041*
O320.8916 (3)0.2031 (2)0.05350 (18)0.0333 (4)
H3210.780 (5)0.218 (4)0.049 (3)0.040*
H3220.871 (5)0.131 (4)0.118 (3)0.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02587 (15)0.02482 (14)0.01988 (14)0.00809 (10)0.01156 (10)0.00671 (10)
Cl10.0310 (3)0.0261 (2)0.0274 (3)0.0059 (2)0.0119 (2)0.00625 (19)
N10.0276 (9)0.0336 (9)0.0199 (8)0.0159 (8)0.0123 (7)0.0122 (7)
C20.0240 (10)0.0195 (8)0.0197 (9)0.0062 (8)0.0101 (8)0.0088 (7)
N30.0262 (9)0.0270 (8)0.0189 (8)0.0142 (7)0.0088 (7)0.0105 (7)
C40.0229 (10)0.0210 (9)0.0188 (9)0.0081 (8)0.0077 (8)0.0070 (7)
C50.0212 (9)0.0254 (9)0.0171 (9)0.0093 (8)0.0076 (7)0.0076 (7)
C60.0210 (9)0.0253 (9)0.0200 (9)0.0083 (8)0.0087 (8)0.0092 (7)
N20.0235 (9)0.0314 (9)0.0185 (8)0.0089 (7)0.0079 (7)0.0114 (7)
C210.0322 (11)0.0261 (10)0.0182 (9)0.0088 (9)0.0118 (9)0.0073 (8)
C220.0256 (10)0.0270 (10)0.0192 (9)0.0086 (8)0.0094 (8)0.0093 (8)
O210.0425 (10)0.0369 (9)0.0315 (9)0.0046 (8)0.0252 (8)0.0052 (7)
O220.0386 (9)0.0245 (7)0.0283 (8)0.0050 (7)0.0195 (7)0.0050 (6)
C30.0466 (15)0.0590 (16)0.0300 (12)0.0397 (13)0.0148 (11)0.0224 (12)
O40.0334 (9)0.0389 (9)0.0245 (8)0.0222 (7)0.0149 (7)0.0117 (6)
N50.0231 (9)0.0295 (9)0.0183 (8)0.0104 (7)0.0075 (7)0.0084 (7)
O50.0336 (9)0.0626 (12)0.0237 (8)0.0280 (9)0.0095 (7)0.0192 (8)
N60.0270 (10)0.0471 (12)0.0236 (9)0.0205 (9)0.0115 (8)0.0150 (8)
O310.0327 (9)0.0309 (9)0.0373 (10)0.0069 (7)0.0194 (8)0.0071 (7)
O320.0347 (9)0.0374 (9)0.0282 (8)0.0161 (8)0.0089 (7)0.0112 (7)
Geometric parameters (Å, º) top
Cu1—Cl12.2813 (6)C6—N61.310 (3)
Cu1—O42.3797 (16)N2—C211.449 (3)
Cu1—N51.9957 (18)N2—H20.82 (3)
Cu1—O52.837 (2)C21—C221.524 (3)
Cu1—O21i2.7445 (19)C21—H21A0.9900
Cu1—O22ii1.9845 (16)C21—H21B0.9900
Cu1—O311.9642 (17)C22—O211.249 (3)
N1—C21.323 (3)C22—O221.258 (3)
C2—N31.375 (3)C3—H3A0.9800
N3—C41.394 (2)C3—H3B0.9800
C4—C51.453 (3)C3—H3C0.9800
C5—C61.440 (3)N6—H6A0.85 (3)
C6—N11.341 (3)N6—H6B0.81 (3)
C2—N21.333 (3)O31—H3110.81 (4)
N3—C31.469 (3)O31—H3120.77 (3)
C4—O41.223 (3)O32—H3210.83 (4)
C5—N51.343 (3)O32—H3220.78 (3)
N5—O51.259 (2)
O31—Cu1—O22ii89.77 (7)C21—N2—H2116.7 (19)
O31—Cu1—N5176.09 (8)N2—C21—C22112.24 (17)
O22ii—Cu1—N586.50 (7)N2—C21—H21A109.2
O31—Cu1—Cl190.95 (6)C22—C21—H21A109.2
O22ii—Cu1—Cl1176.79 (6)N2—C21—H21B109.2
N5—Cu1—Cl192.84 (6)C22—C21—H21B109.2
O31—Cu1—O4103.26 (7)H21A—C21—H21B107.9
O22ii—Cu1—O487.62 (7)O21—C22—O22126.4 (2)
N5—Cu1—O475.44 (6)O21—C22—C21117.10 (19)
Cl1—Cu1—O495.26 (5)O22—C22—C21116.50 (18)
C2—N1—C6118.87 (18)C22—O22—Cu1ii129.82 (15)
N1—C2—N2117.75 (18)N3—C3—H3A109.5
N1—C2—N3125.00 (18)N3—C3—H3B109.5
N2—C2—N3117.25 (18)H3A—C3—H3B109.5
C2—N3—C4120.28 (17)N3—C3—H3C109.5
C2—N3—C3121.40 (17)H3A—C3—H3C109.5
C4—N3—C3118.13 (18)H3B—C3—H3C109.5
O4—C4—N3121.09 (19)C4—O4—Cu1106.30 (13)
O4—C4—C5123.75 (19)O5—N5—C5120.48 (18)
N3—C4—C5115.16 (17)O5—N5—Cu1119.57 (14)
N5—C5—C6125.85 (18)C5—N5—Cu1119.94 (14)
N5—C5—C4114.32 (18)C6—N6—H6A115 (2)
C6—C5—C4119.80 (18)C6—N6—H6B115 (2)
N6—C6—N1118.04 (19)H6A—N6—H6B129 (3)
N6—C6—C5121.52 (19)Cu1—O31—H311119 (2)
N1—C6—C5120.42 (18)Cu1—O31—H312104 (3)
C2—N2—C21121.78 (18)H311—O31—H312113 (3)
C2—N2—H2120.2 (19)H321—O32—H322110 (3)
C6—N1—C2—N2173.90 (18)C2—N2—C21—C2281.3 (2)
C6—N1—C2—N35.4 (3)N2—C21—C22—O21166.4 (2)
N1—C2—N3—C48.6 (3)N2—C21—C22—O2212.9 (3)
N2—C2—N3—C4170.67 (18)O21—C22—O22—Cu1ii9.6 (4)
N1—C2—N3—C3176.5 (2)C21—C22—O22—Cu1ii171.23 (15)
N2—C2—N3—C34.2 (3)N3—C4—O4—Cu1175.63 (15)
C2—N3—C4—O4175.40 (19)C5—C4—O4—Cu15.0 (2)
C3—N3—C4—O40.4 (3)O31—Cu1—O4—C4179.41 (14)
C2—N3—C4—C55.2 (3)O22ii—Cu1—O4—C491.38 (15)
C3—N3—C4—C5179.7 (2)N5—Cu1—O4—C44.38 (14)
O4—C4—C5—N52.8 (3)Cl1—Cu1—O4—C487.19 (14)
N3—C4—C5—N5177.87 (17)C6—C5—N5—O53.6 (3)
O4—C4—C5—C6179.08 (19)C4—C5—N5—O5178.34 (19)
N3—C4—C5—C60.3 (3)C6—C5—N5—Cu1175.91 (15)
C2—N1—C6—N6178.8 (2)C4—C5—N5—Cu12.1 (2)
C2—N1—C6—C50.7 (3)O22ii—Cu1—N5—O588.61 (18)
N5—C5—C6—N63.5 (3)Cl1—Cu1—N5—O588.24 (17)
C4—C5—C6—N6178.6 (2)O4—Cu1—N5—O5177.06 (18)
N5—C5—C6—N1174.6 (2)O22ii—Cu1—N5—C591.83 (17)
C4—C5—C6—N13.3 (3)Cl1—Cu1—N5—C591.32 (16)
N1—C2—N2—C2119.5 (3)O4—Cu1—N5—C53.38 (15)
N3—C2—N2—C21161.19 (18)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O32iii0.82 (3)2.13 (3)2.829 (3)144 (3)
N6—H6A···Cl1iv0.85 (3)2.58 (4)3.382 (2)158 (3)
N6—H6B···Cl1v0.81 (3)2.91 (4)3.466 (2)128 (3)
N6—H6B···O50.81 (3)2.02 (3)2.658 (3)135 (3)
O31—H311···O32vi0.81 (4)1.97 (4)2.779 (3)177 (4)
O31—H312···O21ii0.77 (3)1.89 (4)2.607 (3)154 (3)
O32—H321···O210.83 (4)1.97 (4)2.775 (3)165 (3)
O32—H322···Cl1vii0.78 (3)2.78 (3)3.358 (2)133 (2)
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x1, y, z; (iv) x+1, y, z+1; (v) x+1, y, z; (vi) x1, y, z+1; (vii) x+1, y, z1.

Experimental details

Crystal data
Chemical formula[Cu(C7H8N5O4)Cl(H2O)]·H2O
Mr361.21
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)6.9807 (5), 9.1462 (6), 11.2512 (6)
α, β, γ (°)107.357 (5), 105.037 (5), 102.028 (6)
V3)629.54 (8)
Z2
Radiation typeMo Kα
µ (mm1)1.98
Crystal size (mm)0.41 × 0.25 × 0.22
Data collection
DiffractometerBruker Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.601, 0.647
No. of measured, independent and
observed [I > 2σ(I)] reflections
3745, 2889, 2569
Rint0.084
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.080, 1.04
No. of reflections2889
No. of parameters203
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.72, 0.66

Computer programs: COLLECT (Hooft, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top
Cu1—Cl12.2813 (6)N3—C41.394 (2)
Cu1—O42.3797 (16)C4—C51.453 (3)
Cu1—N51.9957 (18)C5—C61.440 (3)
Cu1—O52.837 (2)C6—N11.341 (3)
Cu1—O21i2.7445 (19)C2—N21.333 (3)
Cu1—O22ii1.9845 (16)C4—O41.223 (3)
Cu1—O311.9642 (17)C5—N51.343 (3)
N1—C21.323 (3)N5—O51.259 (2)
C2—N31.375 (3)C6—N61.310 (3)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O32iii0.82 (3)2.13 (3)2.829 (3)144 (3)
N6—H6A···Cl1iv0.85 (3)2.58 (4)3.382 (2)158 (3)
N6—H6B···Cl1v0.81 (3)2.91 (4)3.466 (2)128 (3)
N6—H6B···O50.81 (3)2.02 (3)2.658 (3)135 (3)
O31—H311···O32vi0.81 (4)1.97 (4)2.779 (3)177 (4)
O31—H312···O21ii0.77 (3)1.89 (4)2.607 (3)154 (3)
O32—H321···O210.83 (4)1.97 (4)2.775 (3)165 (3)
O32—H322···Cl1vii0.78 (3)2.78 (3)3.358 (2)133 (2)
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x1, y, z; (iv) x+1, y, z+1; (v) x+1, y, z; (vi) x1, y, z+1; (vii) x+1, y, z1.
 

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