metal-organic compounds
[Aquabis(nitrato-κO)copper(II)]-μ-{bis[5-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl]selenide}-[diaqua(nitrato-κO)copper(II)] nitrate monohydrate
aDepartment of Chemistry, National Taras Shevchenko University, Volodymyrska Street 64, 01601 Kyiv, Ukraine, bInstitut de Ciencia Molecular (ICMol), Departament de Quimica Inorganica, Universitat de Valencia, C/ Catedratico Jose Beltran Martinez, 2, 46980 Paterna (Valencia), Spain, and cFaculty of Chemistry, University of Wroclaw, 14, F. Joliot–Curie Street, 50383 Wroclaw, Poland
*Correspondence e-mail: pavlenko_vadim@univ.kiev.ua
In the title binuclear complex, [Cu2(NO3)3(C18H16N6Se)(H2O)3]NO3·H2O, the CuII ions are pentacoordinated in a tetragonal–pyramidal geometry. In both cases, the equatorial planes are formed by a chelating pyrazole-pyridine group, a water molecule and a nitrate O atom, whereas the apical positions are occupied by a water molecule for one CuII ion and a nitrate O atom for the other. The organic selenide ligand adopts a trans configuration with respect to the C–Se–C plane. Numerous intermolecular O—H⋯O and N—H⋯O hydrogen bonds between the coordinating and lattice water molecules, nitrate anions and pyrazole groups are observed. π–π stacking interactions between the pyridine rings [averaged centroid–centroid distance = 3.652 (5) Å] are also present. The lattice water molecule is equally disordered over two sets of sites.
Related literature
For details and applications of related pyrazole compounds, see: Fritsky et al. (2003); Kovbasyuk et al. (2004); Krämer et al. (2002); Krämer & Fritsky (2000); Penkova et al. (2009); Sachse et al. (2008). For structural studies of related pyrazolylselenides, see: Seredyuk et al. (2010a, 2011, 2012). For structural studies of d-metal complexes with bis(3,5-dimethyl-1H-pyrazol-4-yl)selenide, see: Seredyuk et al. (2007, 2009, 2010b,c). For related structures, see: Fritsky et al. (2004); Kanderal et al. (2005); Moroz et al. (2010, 2012). For the treatment of disordered water molecules, see: Nardelli (1999).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812045217/hy2595sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812045217/hy2595Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812045217/hy2595Isup3.cdx
Supporting information file. DOI: 10.1107/S1600536812045217/hy2595Isup4.cdx
In a solution of Cu(NO3)2.6H2O (0.144 g, 0.468 mmol) in 5 ml of water a batch of bis[3-methyl-5-(pyridin-2-yl)-1H-pyrazol-4-yl]selenide methanol monosolvate (0.1 g, 0.234 mmol) (Seredyuk et al., 2010a) was dissolved. After several weeks,well formed blue-green crystals were formed and isolated. Analysis, calculated for C18H26Cu2N9O14Se: C 27.07, H 3.28, N 15.79%; found: C 27.15, H 3.14, N 15.70%.
H atoms on NH groups and the coordinated water molecules were located from a difference Fourier map and constrained to ride on their parent atoms, with Uiso(H) = 1.2 or 1.5Ueq(N, O). One of the H atoms attached to the coordinated water molecule O9 was found to be disordered over two positions with an occupancy ratio of 0.5:0.5 (as O9 forms a hydrogen bond with its symmetry-related water molecule through H2O9, which limits the occupancy by 1/2). Lattice water molecule was found to be disordered over two sites (O1WA and O1WB), with an occupancy ratio of 0.5:0.5. O1WA and O1WB were restrained with effective standard deviation 0.01 so that its Uij components approximate to isotropic behavior. H atoms of the disordered water molecule were placed at calculated positions (Nardelli, 1999) and refined as riding in as-found relative positions with Uiso(H) = 1.5Ueq(O). C-bound H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (CH) and 0.96 (CH3) Å and Uiso(H) = 1.2(1.5 for methyl)Ueq(C). Noticeable thermal vibrations of O atoms were observed in some of the nitrate anions, so that geometric constraints were placed on some of the nitrate O atoms to improve their geometries and thermal ellipsoid parameters. The highest residual electron density was found 0.88 Å from O7, and the deepest hole 0.27 Å from O7.
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids. Hydrogen bonds are indicated by dashed lines. H atoms are omitted for clarity. [Symmetry codes: (i) x, y, -1+z; (ii) 1-x, -y, 1-z; (iii) -x, -y, 1-z.] | |
Fig. 2. A part of the crystal packing showing π–π stacking interactions between the pyridine rings (dashed lines). |
[Cu2(NO3)3(C18H16N6Se)(H2O)3]NO3·H2O | Z = 2 |
Mr = 842.51 | F(000) = 844 |
Triclinic, P1 | Dx = 1.889 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.102 (2) Å | Cell parameters from 6135 reflections |
b = 11.629 (2) Å | θ = 3.5–28.4° |
c = 12.796 (3) Å | µ = 2.76 mm−1 |
α = 98.56 (3)° | T = 100 K |
β = 93.07 (3)° | Block, green |
γ = 93.04 (3)° | 0.27 × 0.23 × 0.13 mm |
V = 1481.5 (5) Å3 |
Bruker APEXII CCD diffractometer | 6511 independent reflections |
Radiation source: fine-focus sealed tube | 5817 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
ϕ and ω scans | θmax = 28.4°, θmin = 3.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.476, Tmax = 0.716 | k = −15→15 |
11167 measured reflections | l = −17→17 |
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)] = 0.080 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.223 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1001P)2] where P = (Fo2 + 2Fc2)/3 |
6511 reflections | (Δ/σ)max = 0.002 |
418 parameters | Δρmax = 2.05 e Å−3 |
39 restraints | Δρmin = −1.35 e Å−3 |
[Cu2(NO3)3(C18H16N6Se)(H2O)3]NO3·H2O | γ = 93.04 (3)° |
Mr = 842.51 | V = 1481.5 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.102 (2) Å | Mo Kα radiation |
b = 11.629 (2) Å | µ = 2.76 mm−1 |
c = 12.796 (3) Å | T = 100 K |
α = 98.56 (3)° | 0.27 × 0.23 × 0.13 mm |
β = 93.07 (3)° |
Bruker APEXII CCD diffractometer | 6511 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5817 reflections with I > 2σ(I) |
Tmin = 0.476, Tmax = 0.716 | Rint = 0.073 |
11167 measured reflections |
R[F2 > 2σ(F2)] = 0.080 | 39 restraints |
wR(F2) = 0.223 | H-atom parameters constrained |
S = 1.02 | Δρmax = 2.05 e Å−3 |
6511 reflections | Δρmin = −1.35 e Å−3 |
418 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Se1 | 0.21129 (9) | 0.43349 (8) | 0.24378 (7) | 0.0235 (3) | |
Cu1 | 0.02084 (10) | 0.23134 (10) | 0.60026 (9) | 0.0206 (3) | |
Cu2 | 0.44191 (10) | 0.14805 (10) | −0.10606 (9) | 0.0216 (3) | |
O1 | 0.5970 (6) | 0.0816 (5) | −0.1753 (5) | 0.0272 (16) | |
H1O1 | 0.5992 | 0.1308 | −0.2182 | 0.041* | |
H2O1 | 0.6854 | 0.0643 | −0.1449 | 0.041* | |
O2 | 0.3959 (6) | 0.2470 (6) | −0.2494 (5) | 0.0316 (16) | |
O3 | 0.4542 (10) | 0.3529 (9) | −0.3672 (9) | 0.0775 (16) | |
O4 | 0.5925 (10) | 0.2392 (9) | −0.3114 (9) | 0.0775 (16) | |
O5 | 0.3321 (6) | 0.0230 (6) | −0.1982 (6) | 0.0372 (18) | |
O6 | 0.3899 (10) | −0.0632 (9) | −0.0650 (10) | 0.0775 (16) | |
O7 | 0.2943 (10) | −0.1626 (9) | −0.2145 (9) | 0.0775 (16) | |
O8 | 0.1528 (6) | 0.1420 (6) | 0.6666 (5) | 0.0258 (15) | |
H1O8 | 0.1165 | 0.0833 | 0.6890 | 0.039* | |
H2O8 | 0.2230 | 0.1798 | 0.7126 | 0.039* | |
O9 | −0.1007 (6) | 0.0624 (6) | 0.5480 (5) | 0.0289 (15) | |
H1O9 | −0.1127 | 0.0330 | 0.6044 | 0.043* | |
H2O9 | −0.0410 | 0.0253 | 0.5155 | 0.043* | 0.50 |
H3O9 | −0.1677 | 0.0810 | 0.5121 | 0.043* | 0.50 |
O10 | −0.0814 (6) | 0.2541 (5) | 0.7294 (5) | 0.0211 (14) | |
O11 | 0.0904 (6) | 0.3763 (5) | 0.7686 (5) | 0.0254 (15) | |
O12 | −0.0468 (7) | 0.3494 (6) | 0.8898 (5) | 0.0302 (16) | |
O13 | −0.1565 (6) | −0.0198 (6) | 0.7310 (5) | 0.0289 (16) | |
O14 | 0.0347 (6) | 0.0339 (6) | 0.8173 (5) | 0.0245 (15) | |
O15 | −0.1499 (6) | 0.0426 (6) | 0.8989 (5) | 0.0266 (15) | |
O1WA | 0.3744 (16) | 0.0262 (14) | 0.5467 (12) | 0.052 (3) | 0.50 |
H1WA | 0.3750 | 0.0219 | 0.6157 | 0.078* | 0.50 |
H2WA | 0.4560 | 0.0074 | 0.5262 | 0.078* | 0.50 |
O1WB | 0.2742 (16) | −0.1094 (14) | 0.6081 (12) | 0.052 (3) | 0.50 |
H1WB | 0.2220 | −0.1701 | 0.5659 | 0.078* | 0.50 |
H2WB | 0.2854 | −0.1259 | 0.6728 | 0.078* | 0.50 |
N1 | 0.2979 (7) | 0.2094 (6) | −0.0216 (6) | 0.0208 (17) | |
N2 | 0.1677 (7) | 0.1782 (6) | −0.0076 (6) | 0.0191 (16) | |
H1N2 | 0.1358 | 0.1221 | −0.0461 | 0.023* | |
N3 | 0.5397 (7) | 0.2878 (6) | −0.0177 (6) | 0.0188 (16) | |
N4 | 0.1334 (7) | 0.2424 (7) | 0.4797 (6) | 0.0222 (17) | |
N5 | 0.2575 (7) | 0.2116 (7) | 0.4554 (6) | 0.0228 (17) | |
H1N | 0.3032 | 0.1655 | 0.4873 | 0.027* | |
N6 | −0.0912 (7) | 0.3259 (7) | 0.5166 (6) | 0.0224 (17) | |
N7 | 0.3367 (10) | −0.0720 (9) | −0.1549 (10) | 0.062 (3) | |
N8 | 0.4817 (9) | 0.2826 (8) | −0.3083 (7) | 0.037 (2) | |
N9 | −0.0101 (7) | 0.3290 (7) | 0.7998 (6) | 0.0243 (18) | |
N10 | −0.0915 (7) | 0.0180 (6) | 0.8146 (6) | 0.0224 (17) | |
C1 | −0.0184 (8) | 0.2275 (8) | 0.1079 (7) | 0.021 (2) | |
H1A | −0.0662 | 0.1677 | 0.0582 | 0.031* | |
H1B | −0.0611 | 0.2994 | 0.1085 | 0.031* | |
H1C | −0.0175 | 0.2055 | 0.1773 | 0.031* | |
C2 | 0.1202 (8) | 0.2428 (8) | 0.0766 (6) | 0.0164 (18) | |
C3 | 0.2234 (9) | 0.3198 (8) | 0.1218 (7) | 0.022 (2) | |
C4 | 0.3337 (8) | 0.2966 (8) | 0.0588 (7) | 0.0184 (18) | |
C5 | 0.4711 (8) | 0.3463 (8) | 0.0583 (7) | 0.0198 (19) | |
C6 | 0.5225 (9) | 0.4453 (7) | 0.1248 (7) | 0.0203 (19) | |
H6 | 0.4725 | 0.4836 | 0.1766 | 0.024* | |
C7 | 0.6512 (8) | 0.4853 (8) | 0.1111 (7) | 0.0213 (19) | |
H7 | 0.6889 | 0.5514 | 0.1547 | 0.026* | |
C8 | 0.7243 (9) | 0.4275 (8) | 0.0331 (7) | 0.024 (2) | |
H8 | 0.8102 | 0.4548 | 0.0232 | 0.029* | |
C9 | 0.6673 (8) | 0.3289 (7) | −0.0294 (7) | 0.0178 (18) | |
H9 | 0.7164 | 0.2890 | −0.0810 | 0.021* | |
C10 | 0.4320 (9) | 0.2365 (10) | 0.3298 (9) | 0.039 (3) | |
H10A | 0.4872 | 0.2059 | 0.3812 | 0.059* | |
H10B | 0.4744 | 0.3068 | 0.3132 | 0.059* | |
H10C | 0.4185 | 0.1802 | 0.2667 | 0.059* | |
C11 | 0.2990 (9) | 0.2627 (8) | 0.3746 (7) | 0.0216 (19) | |
C12 | 0.1988 (9) | 0.3295 (7) | 0.3456 (7) | 0.0189 (19) | |
C13 | 0.0964 (8) | 0.3147 (8) | 0.4154 (7) | 0.021 (2) | |
C14 | −0.0378 (8) | 0.3594 (8) | 0.4312 (7) | 0.0181 (18) | |
C15 | −0.1049 (9) | 0.4238 (8) | 0.3645 (7) | 0.024 (2) | |
H15 | −0.0666 | 0.4441 | 0.3048 | 0.029* | |
C16 | −0.2299 (9) | 0.4566 (8) | 0.3895 (8) | 0.024 (2) | |
H16 | −0.2769 | 0.5015 | 0.3478 | 0.029* | |
C17 | −0.2853 (9) | 0.4213 (8) | 0.4786 (8) | 0.027 (2) | |
H17 | −0.3695 | 0.4428 | 0.4964 | 0.032* | |
C18 | −0.2157 (8) | 0.3552 (8) | 0.5394 (7) | 0.021 (2) | |
H18 | −0.2542 | 0.3300 | 0.5971 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.0247 (5) | 0.0220 (5) | 0.0236 (5) | −0.0016 (4) | 0.0123 (4) | 0.0003 (4) |
Cu1 | 0.0187 (6) | 0.0248 (6) | 0.0192 (6) | 0.0027 (5) | 0.0057 (4) | 0.0040 (5) |
Cu2 | 0.0157 (6) | 0.0244 (6) | 0.0249 (6) | 0.0036 (5) | 0.0069 (5) | 0.0016 (5) |
O1 | 0.016 (3) | 0.030 (4) | 0.035 (4) | 0.008 (3) | 0.009 (3) | −0.002 (3) |
O2 | 0.022 (4) | 0.041 (4) | 0.034 (4) | 0.004 (3) | 0.010 (3) | 0.009 (3) |
O3 | 0.069 (3) | 0.074 (3) | 0.101 (4) | 0.022 (3) | 0.039 (3) | 0.032 (3) |
O4 | 0.069 (3) | 0.074 (3) | 0.101 (4) | 0.022 (3) | 0.039 (3) | 0.032 (3) |
O5 | 0.023 (4) | 0.027 (4) | 0.059 (5) | 0.007 (3) | 0.008 (3) | −0.007 (4) |
O6 | 0.069 (3) | 0.074 (3) | 0.101 (4) | 0.022 (3) | 0.039 (3) | 0.032 (3) |
O7 | 0.069 (3) | 0.074 (3) | 0.101 (4) | 0.022 (3) | 0.039 (3) | 0.032 (3) |
O8 | 0.021 (3) | 0.035 (4) | 0.023 (4) | 0.004 (3) | 0.002 (3) | 0.008 (3) |
O9 | 0.034 (4) | 0.029 (4) | 0.022 (4) | 0.004 (3) | −0.001 (3) | −0.003 (3) |
O10 | 0.023 (3) | 0.025 (3) | 0.014 (3) | −0.002 (3) | 0.001 (3) | −0.003 (3) |
O11 | 0.019 (3) | 0.028 (4) | 0.030 (4) | −0.001 (3) | 0.006 (3) | 0.005 (3) |
O12 | 0.037 (4) | 0.039 (4) | 0.015 (3) | 0.012 (3) | 0.013 (3) | −0.001 (3) |
O13 | 0.029 (4) | 0.038 (4) | 0.018 (4) | −0.005 (3) | 0.006 (3) | 0.002 (3) |
O14 | 0.011 (3) | 0.035 (4) | 0.027 (4) | 0.003 (3) | 0.005 (3) | 0.005 (3) |
O15 | 0.026 (4) | 0.036 (4) | 0.018 (3) | 0.006 (3) | 0.009 (3) | 0.001 (3) |
O1WA | 0.063 (6) | 0.054 (5) | 0.036 (5) | 0.032 (5) | −0.013 (4) | −0.008 (4) |
O1WB | 0.063 (6) | 0.054 (5) | 0.036 (5) | 0.032 (5) | −0.013 (4) | −0.008 (4) |
N1 | 0.007 (3) | 0.026 (4) | 0.029 (4) | 0.002 (3) | 0.004 (3) | 0.001 (3) |
N2 | 0.017 (4) | 0.018 (4) | 0.023 (4) | 0.000 (3) | 0.008 (3) | 0.003 (3) |
N3 | 0.012 (4) | 0.022 (4) | 0.023 (4) | 0.003 (3) | 0.005 (3) | 0.003 (3) |
N4 | 0.016 (4) | 0.023 (4) | 0.028 (4) | 0.004 (3) | 0.007 (3) | 0.003 (3) |
N5 | 0.014 (4) | 0.029 (4) | 0.024 (4) | 0.000 (3) | 0.000 (3) | 0.002 (3) |
N6 | 0.014 (4) | 0.026 (4) | 0.027 (4) | 0.005 (3) | 0.004 (3) | 0.003 (3) |
N7 | 0.036 (5) | 0.047 (6) | 0.094 (7) | −0.010 (5) | 0.026 (5) | −0.022 (6) |
N8 | 0.041 (6) | 0.035 (5) | 0.038 (5) | 0.007 (4) | 0.013 (4) | 0.011 (4) |
N9 | 0.015 (4) | 0.027 (4) | 0.032 (5) | 0.004 (3) | 0.002 (3) | 0.005 (4) |
N10 | 0.021 (4) | 0.020 (4) | 0.028 (5) | 0.002 (3) | 0.010 (3) | 0.006 (3) |
C1 | 0.007 (4) | 0.036 (5) | 0.019 (5) | 0.009 (4) | 0.006 (3) | −0.001 (4) |
C2 | 0.006 (4) | 0.030 (5) | 0.013 (4) | 0.002 (3) | −0.001 (3) | 0.000 (4) |
C3 | 0.023 (5) | 0.027 (5) | 0.016 (5) | 0.000 (4) | 0.013 (4) | 0.002 (4) |
C4 | 0.016 (4) | 0.026 (5) | 0.014 (4) | 0.004 (4) | 0.010 (3) | 0.004 (3) |
C5 | 0.012 (4) | 0.029 (5) | 0.021 (5) | 0.000 (4) | 0.006 (4) | 0.008 (4) |
C6 | 0.021 (5) | 0.019 (5) | 0.021 (5) | 0.008 (4) | 0.003 (4) | 0.003 (4) |
C7 | 0.013 (4) | 0.021 (5) | 0.027 (5) | −0.003 (4) | 0.000 (4) | −0.002 (4) |
C8 | 0.019 (5) | 0.023 (5) | 0.032 (6) | −0.004 (4) | 0.009 (4) | 0.005 (4) |
C9 | 0.012 (4) | 0.022 (5) | 0.019 (5) | 0.006 (3) | 0.002 (3) | 0.001 (4) |
C10 | 0.016 (5) | 0.065 (8) | 0.039 (7) | 0.009 (5) | 0.016 (5) | 0.011 (6) |
C11 | 0.019 (5) | 0.023 (5) | 0.022 (5) | −0.001 (4) | 0.004 (4) | 0.000 (4) |
C12 | 0.022 (5) | 0.018 (5) | 0.016 (4) | −0.005 (4) | 0.010 (4) | −0.002 (3) |
C13 | 0.012 (4) | 0.022 (5) | 0.026 (5) | −0.004 (4) | 0.005 (4) | 0.000 (4) |
C14 | 0.017 (4) | 0.022 (5) | 0.013 (4) | −0.003 (4) | 0.004 (3) | −0.005 (3) |
C15 | 0.023 (5) | 0.027 (5) | 0.022 (5) | 0.001 (4) | 0.009 (4) | −0.002 (4) |
C16 | 0.019 (5) | 0.027 (5) | 0.030 (5) | 0.007 (4) | 0.007 (4) | 0.014 (4) |
C17 | 0.021 (5) | 0.032 (6) | 0.028 (5) | 0.007 (4) | 0.014 (4) | 0.003 (4) |
C18 | 0.016 (4) | 0.026 (5) | 0.019 (5) | −0.007 (4) | 0.003 (4) | 0.002 (4) |
Se1—C3 | 1.903 (9) | N3—C5 | 1.348 (10) |
Se1—C12 | 1.909 (9) | N3—C9 | 1.374 (10) |
Cu1—O8 | 1.966 (6) | N4—C13 | 1.315 (11) |
Cu1—N4 | 1.980 (7) | N4—N5 | 1.361 (10) |
Cu1—O10 | 1.988 (6) | N5—C11 | 1.342 (11) |
Cu1—N6 | 1.998 (7) | N5—H1N | 0.8600 |
Cu1—O9 | 2.254 (7) | N6—C14 | 1.342 (11) |
Cu2—N1 | 1.961 (7) | N6—C18 | 1.356 (10) |
Cu2—O1 | 1.978 (6) | C1—C2 | 1.486 (11) |
Cu2—O5 | 1.979 (7) | C1—H1A | 0.9600 |
Cu2—N3 | 2.015 (7) | C1—H1B | 0.9600 |
Cu2—O2 | 2.345 (7) | C1—H1C | 0.9600 |
O1—H1O1 | 0.8502 | C2—C3 | 1.380 (12) |
O1—H2O1 | 0.9965 | C3—C4 | 1.425 (11) |
O2—N8 | 1.270 (10) | C4—C5 | 1.476 (11) |
O3—N8 | 1.225 (12) | C5—C6 | 1.384 (12) |
O4—N8 | 1.252 (12) | C6—C7 | 1.386 (12) |
O5—N7 | 1.309 (12) | C6—H6 | 0.9300 |
O6—N7 | 1.231 (12) | C7—C8 | 1.389 (12) |
O7—N7 | 1.247 (12) | C7—H7 | 0.9300 |
O8—H1O8 | 0.8521 | C8—C9 | 1.376 (12) |
O8—H2O8 | 0.9420 | C8—H8 | 0.9300 |
O9—H1O9 | 0.8544 | C9—H9 | 0.9300 |
O9—H2O9 | 0.8510 | C10—C11 | 1.516 (12) |
O9—H3O9 | 0.8534 | C10—H10A | 0.9600 |
O10—N9 | 1.311 (9) | C10—H10B | 0.9600 |
O11—N9 | 1.242 (9) | C10—H10C | 0.9600 |
O12—N9 | 1.222 (9) | C11—C12 | 1.377 (12) |
O13—N10 | 1.233 (10) | C12—C13 | 1.423 (11) |
O14—N10 | 1.276 (9) | C13—C14 | 1.490 (11) |
O15—N10 | 1.261 (9) | C14—C15 | 1.390 (13) |
O1WA—H1WA | 0.8913 | C15—C16 | 1.379 (12) |
O1WA—H2WA | 0.9065 | C15—H15 | 0.9300 |
O1WB—H1WB | 0.9407 | C16—C17 | 1.402 (12) |
O1WB—H2WB | 0.8807 | C16—H16 | 0.9300 |
N1—C4 | 1.352 (11) | C17—C18 | 1.366 (13) |
N1—N2 | 1.373 (9) | C17—H17 | 0.9300 |
N2—C2 | 1.344 (10) | C18—H18 | 0.9300 |
N2—H1N2 | 0.7989 | ||
C3—Se1—C12 | 97.9 (4) | O11—N9—O10 | 116.5 (7) |
O8—Cu1—N4 | 91.0 (3) | O13—N10—O15 | 119.9 (7) |
O8—Cu1—O10 | 92.5 (3) | O13—N10—O14 | 121.1 (7) |
N4—Cu1—O10 | 168.5 (3) | O15—N10—O14 | 119.0 (8) |
O8—Cu1—N6 | 170.8 (3) | C2—C1—H1A | 109.5 |
N4—Cu1—N6 | 79.9 (3) | C2—C1—H1B | 109.5 |
O10—Cu1—N6 | 96.1 (3) | H1A—C1—H1B | 109.5 |
O8—Cu1—O9 | 88.0 (3) | C2—C1—H1C | 109.5 |
N4—Cu1—O9 | 102.8 (3) | H1A—C1—H1C | 109.5 |
O10—Cu1—O9 | 88.3 (2) | H1B—C1—H1C | 109.5 |
N6—Cu1—O9 | 95.3 (3) | N2—C2—C3 | 106.4 (7) |
N1—Cu2—O1 | 173.1 (3) | N2—C2—C1 | 123.3 (8) |
N1—Cu2—O5 | 96.5 (3) | C3—C2—C1 | 130.3 (8) |
O1—Cu2—O5 | 86.7 (3) | C2—C3—C4 | 106.5 (8) |
N1—Cu2—N3 | 80.1 (3) | C2—C3—Se1 | 124.5 (6) |
O1—Cu2—N3 | 97.3 (3) | C4—C3—Se1 | 129.1 (7) |
O5—Cu2—N3 | 173.7 (3) | N1—C4—C3 | 109.3 (8) |
N1—Cu2—O2 | 96.1 (3) | N1—C4—C5 | 114.7 (7) |
O1—Cu2—O2 | 90.4 (3) | C3—C4—C5 | 136.0 (8) |
O5—Cu2—O2 | 81.3 (3) | N3—C5—C6 | 123.4 (8) |
N3—Cu2—O2 | 93.7 (3) | N3—C5—C4 | 112.4 (8) |
Cu2—O1—H1O1 | 93.2 | C6—C5—C4 | 124.1 (8) |
Cu2—O1—H2O1 | 131.0 | C5—C6—C7 | 117.5 (8) |
H1O1—O1—H2O1 | 115.1 | C5—C6—H6 | 121.3 |
N8—O2—Cu2 | 125.3 (6) | C7—C6—H6 | 121.3 |
N7—O5—Cu2 | 108.0 (7) | C6—C7—C8 | 120.6 (8) |
Cu1—O8—H1O8 | 111.7 | C6—C7—H7 | 119.7 |
Cu1—O8—H2O8 | 121.2 | C8—C7—H7 | 119.7 |
H1O8—O8—H2O8 | 113.1 | C9—C8—C7 | 118.8 (8) |
Cu1—O9—H1O9 | 105.7 | C9—C8—H8 | 120.6 |
Cu1—O9—H2O9 | 97.5 | C7—C8—H8 | 120.6 |
H1O9—O9—H2O9 | 107.5 | N3—C9—C8 | 121.8 (8) |
Cu1—O9—H3O9 | 104.7 | N3—C9—H9 | 119.1 |
H1O9—O9—H3O9 | 119.4 | C8—C9—H9 | 119.1 |
H2O9—O9—H3O9 | 118.8 | C11—C10—H10A | 109.5 |
N9—O10—Cu1 | 106.7 (5) | C11—C10—H10B | 109.5 |
H1WA—O1WA—H2WA | 106.2 | H10A—C10—H10B | 109.5 |
H1WB—O1WB—H2WB | 109.3 | C11—C10—H10C | 109.5 |
C4—N1—N2 | 105.2 (7) | H10A—C10—H10C | 109.5 |
C4—N1—Cu2 | 115.9 (5) | H10B—C10—H10C | 109.5 |
N2—N1—Cu2 | 137.9 (6) | N5—C11—C12 | 107.0 (7) |
C2—N2—N1 | 112.7 (7) | N5—C11—C10 | 120.4 (8) |
C2—N2—H1N2 | 130.9 | C12—C11—C10 | 132.5 (9) |
N1—N2—H1N2 | 116.0 | C11—C12—C13 | 105.7 (8) |
C5—N3—C9 | 118.0 (7) | C11—C12—Se1 | 124.9 (6) |
C5—N3—Cu2 | 115.9 (6) | C13—C12—Se1 | 129.0 (7) |
C9—N3—Cu2 | 126.1 (6) | N4—C13—C12 | 109.1 (8) |
C13—N4—N5 | 107.3 (7) | N4—C13—C14 | 115.0 (7) |
C13—N4—Cu1 | 115.8 (6) | C12—C13—C14 | 135.9 (9) |
N5—N4—Cu1 | 135.4 (6) | N6—C14—C15 | 122.6 (8) |
C11—N5—N4 | 110.9 (7) | N6—C14—C13 | 112.0 (8) |
C11—N5—H1N | 124.5 | C15—C14—C13 | 125.3 (8) |
N4—N5—H1N | 124.6 | C16—C15—C14 | 118.0 (8) |
C14—N6—C18 | 119.4 (8) | C16—C15—H15 | 121.0 |
C14—N6—Cu1 | 116.2 (6) | C14—C15—H15 | 121.0 |
C18—N6—Cu1 | 124.4 (6) | C15—C16—C17 | 119.1 (9) |
O6—N7—O7 | 127.9 (13) | C15—C16—H16 | 120.4 |
O6—N7—O5 | 117.4 (10) | C17—C16—H16 | 120.4 |
O7—N7—O5 | 114.4 (12) | C18—C17—C16 | 120.1 (8) |
O3—N8—O4 | 119.6 (10) | C18—C17—H17 | 120.0 |
O3—N8—O2 | 120.7 (9) | C16—C17—H17 | 120.0 |
O4—N8—O2 | 119.5 (9) | N6—C18—C17 | 120.8 (8) |
O12—N9—O11 | 124.5 (8) | N6—C18—H18 | 119.6 |
O12—N9—O10 | 119.0 (7) | C17—C18—H18 | 119.6 |
N1—Cu2—O2—N8 | 148.5 (7) | N2—N1—C4—C3 | −0.7 (9) |
O1—Cu2—O2—N8 | −29.2 (7) | Cu2—N1—C4—C3 | −171.5 (6) |
O5—Cu2—O2—N8 | −115.8 (7) | N2—N1—C4—C5 | −178.7 (7) |
N3—Cu2—O2—N8 | 68.1 (7) | Cu2—N1—C4—C5 | 10.6 (10) |
N1—Cu2—O5—N7 | −92.2 (6) | C2—C3—C4—N1 | 0.3 (10) |
O1—Cu2—O5—N7 | 81.7 (6) | Se1—C3—C4—N1 | −179.0 (7) |
O2—Cu2—O5—N7 | 172.6 (6) | C2—C3—C4—C5 | 177.7 (10) |
O8—Cu1—O10—N9 | 72.0 (5) | Se1—C3—C4—C5 | −1.7 (16) |
N4—Cu1—O10—N9 | −35.9 (16) | C9—N3—C5—C6 | 0.1 (13) |
N6—Cu1—O10—N9 | −105.0 (5) | Cu2—N3—C5—C6 | −178.8 (7) |
O9—Cu1—O10—N9 | 159.9 (5) | C9—N3—C5—C4 | 177.1 (7) |
O5—Cu2—N1—C4 | 176.4 (6) | Cu2—N3—C5—C4 | −1.9 (9) |
N3—Cu2—N1—C4 | −9.0 (6) | N1—C4—C5—N3 | −5.5 (11) |
O2—Cu2—N1—C4 | −101.7 (6) | C3—C4—C5—N3 | 177.2 (10) |
O5—Cu2—N1—N2 | 9.8 (9) | N1—C4—C5—C6 | 171.4 (8) |
N3—Cu2—N1—N2 | −175.5 (9) | C3—C4—C5—C6 | −5.8 (16) |
O2—Cu2—N1—N2 | 91.7 (9) | N3—C5—C6—C7 | 0.1 (13) |
C4—N1—N2—C2 | 0.9 (9) | C4—C5—C6—C7 | −176.5 (8) |
Cu2—N1—N2—C2 | 168.4 (7) | C5—C6—C7—C8 | 0.3 (13) |
N1—Cu2—N3—C5 | 5.8 (6) | C6—C7—C8—C9 | −0.9 (14) |
O1—Cu2—N3—C5 | −167.8 (6) | C5—N3—C9—C8 | −0.8 (12) |
O2—Cu2—N3—C5 | 101.3 (6) | Cu2—N3—C9—C8 | 178.0 (7) |
N1—Cu2—N3—C9 | −173.1 (7) | C7—C8—C9—N3 | 1.2 (13) |
O1—Cu2—N3—C9 | 13.4 (7) | N4—N5—C11—C12 | 0.3 (10) |
O2—Cu2—N3—C9 | −77.5 (7) | N4—N5—C11—C10 | −176.9 (8) |
O8—Cu1—N4—C13 | −169.3 (7) | N5—C11—C12—C13 | 0.4 (10) |
O10—Cu1—N4—C13 | −61.3 (17) | C10—C11—C12—C13 | 177.2 (10) |
N6—Cu1—N4—C13 | 9.3 (6) | N5—C11—C12—Se1 | 173.5 (6) |
O9—Cu1—N4—C13 | 102.5 (7) | C10—C11—C12—Se1 | −9.8 (15) |
O8—Cu1—N4—N5 | −5.6 (8) | C3—Se1—C12—C11 | 67.1 (8) |
O10—Cu1—N4—N5 | 102.4 (15) | C3—Se1—C12—C13 | −121.5 (8) |
N6—Cu1—N4—N5 | 173.0 (9) | N5—N4—C13—C12 | 1.2 (10) |
O9—Cu1—N4—N5 | −93.7 (8) | Cu1—N4—C13—C12 | 169.3 (6) |
C13—N4—N5—C11 | −1.0 (10) | N5—N4—C13—C14 | −179.3 (7) |
Cu1—N4—N5—C11 | −165.6 (7) | Cu1—N4—C13—C14 | −11.2 (10) |
N4—Cu1—N6—C14 | −5.6 (6) | C11—C12—C13—N4 | −1.0 (10) |
O10—Cu1—N6—C14 | 163.4 (6) | Se1—C12—C13—N4 | −173.7 (7) |
O9—Cu1—N6—C14 | −107.7 (6) | C11—C12—C13—C14 | 179.6 (10) |
N4—Cu1—N6—C18 | 172.9 (8) | Se1—C12—C13—C14 | 6.9 (15) |
O10—Cu1—N6—C18 | −18.0 (7) | C18—N6—C14—C15 | 0.2 (13) |
O9—Cu1—N6—C18 | 70.8 (7) | Cu1—N6—C14—C15 | 178.9 (7) |
Cu2—O5—N7—O6 | 8.7 (12) | C18—N6—C14—C13 | −177.2 (7) |
Cu2—O5—N7—O7 | −166.3 (8) | Cu1—N6—C14—C13 | 1.5 (9) |
Cu2—O2—N8—O3 | −165.3 (8) | N4—C13—C14—N6 | 6.3 (11) |
Cu2—O2—N8—O4 | 19.6 (13) | C12—C13—C14—N6 | −174.4 (9) |
Cu1—O10—N9—O12 | −173.5 (6) | N4—C13—C14—C15 | −171.0 (9) |
Cu1—O10—N9—O11 | 7.8 (8) | C12—C13—C14—C15 | 8.4 (16) |
N1—N2—C2—C3 | −0.7 (10) | N6—C14—C15—C16 | 1.7 (14) |
N1—N2—C2—C1 | 179.2 (8) | C13—C14—C15—C16 | 178.7 (8) |
N2—C2—C3—C4 | 0.2 (10) | C14—C15—C16—C17 | −1.7 (14) |
C1—C2—C3—C4 | −179.6 (9) | C15—C16—C17—C18 | −0.1 (14) |
N2—C2—C3—Se1 | 179.6 (6) | C14—N6—C18—C17 | −2.1 (13) |
C1—C2—C3—Se1 | −0.3 (14) | Cu1—N6—C18—C17 | 179.4 (7) |
C12—Se1—C3—C2 | 70.2 (8) | C16—C17—C18—N6 | 2.0 (14) |
C12—Se1—C3—C4 | −110.6 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O4 | 0.85 | 1.86 | 2.710 (12) | 176 |
O1—H2O1···O15i | 1.00 | 1.77 | 2.763 (9) | 174 |
O8—H1O8···O14 | 0.85 | 2.02 | 2.744 (9) | 142 |
O8—H2O8···O2ii | 0.94 | 1.88 | 2.772 (9) | 156 |
O9—H1O9···O13 | 0.85 | 1.88 | 2.732 (9) | 173 |
O9—H2O9···O9iii | 0.85 | 1.94 | 2.794 (9) | 175 |
O9—H3O9···O1WAiii | 0.85 | 2.40 | 3.024 (18) | 131 |
O9—H3O9···O1WBiii | 0.85 | 1.91 | 2.723 (16) | 159 |
N2—H1N2···O14iv | 0.80 | 2.08 | 2.822 (10) | 155 |
N5—H1N···O1WA | 0.86 | 2.04 | 2.878 (18) | 166 |
O1WA—H1WA···O5ii | 0.89 | 2.44 | 3.320 (17) | 169 |
O1WA—H2WA···O1WAv | 0.91 | 2.02 | 2.92 (3) | 169 |
O1WB—H2WB···O7ii | 0.88 | 1.56 | 2.441 (19) | 175 |
Symmetry codes: (i) x+1, y, z−1; (ii) x, y, z+1; (iii) −x, −y, −z+1; (iv) x, y, z−1; (v) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Cu2(NO3)3(C18H16N6Se)(H2O)3]NO3·H2O |
Mr | 842.51 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 10.102 (2), 11.629 (2), 12.796 (3) |
α, β, γ (°) | 98.56 (3), 93.07 (3), 93.04 (3) |
V (Å3) | 1481.5 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.76 |
Crystal size (mm) | 0.27 × 0.23 × 0.13 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.476, 0.716 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11167, 6511, 5817 |
Rint | 0.073 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.080, 0.223, 1.02 |
No. of reflections | 6511 |
No. of parameters | 418 |
No. of restraints | 39 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.05, −1.35 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O4 | 0.85 | 1.86 | 2.710 (12) | 176 |
O1—H2O1···O15i | 1.00 | 1.77 | 2.763 (9) | 174 |
O8—H1O8···O14 | 0.85 | 2.02 | 2.744 (9) | 142 |
O8—H2O8···O2ii | 0.94 | 1.88 | 2.772 (9) | 156 |
O9—H1O9···O13 | 0.85 | 1.88 | 2.732 (9) | 173 |
O9—H2O9···O9iii | 0.85 | 1.94 | 2.794 (9) | 175 |
O9—H3O9···O1WAiii | 0.85 | 2.40 | 3.024 (18) | 131 |
O9—H3O9···O1WBiii | 0.85 | 1.91 | 2.723 (16) | 159 |
N2—H1N2···O14iv | 0.80 | 2.08 | 2.822 (10) | 155 |
N5—H1N···O1WA | 0.86 | 2.04 | 2.878 (18) | 166 |
O1WA—H1WA···O5ii | 0.89 | 2.44 | 3.320 (17) | 169 |
O1WA—H2WA···O1WAv | 0.91 | 2.02 | 2.92 (3) | 169 |
O1WB—H2WB···O7ii | 0.88 | 1.56 | 2.441 (19) | 175 |
Symmetry codes: (i) x+1, y, z−1; (ii) x, y, z+1; (iii) −x, −y, −z+1; (iv) x, y, z−1; (v) −x+1, −y, −z+1. |
Acknowledgements
Financial support from the State Fund for Fundamental Researches of Ukraine (grant No. F40.3/041) and the Swedish Institute (Visby Program) is gratefully acknowledged. MS thanks the EU for a Marie Curie fellowship (IIF-253254). We also thank Professor Igor O. Fritsky for helpful discussions.
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Pyrazole-derived ligands are widely used in molecular magnetism, bioinorganic modelling and supramolecular chemistry due to their bridging nature and possibility for easy functionalization (Fritsky et al., 2003; Kovbasyuk et al., 2004; Krämer & Fritsky, 2000; Krämer et al., 2002; Penkova et al., 2009; Sachse et al., 2008). As a part of our synthetic and structural study of pyrazolylselenides (Seredyuk et al., 2010a, 2011, 2012) and their complexes with d-metals (Seredyuk et al., 2007, 2009, 2010b, c), we report here the crystal structure of the title compound.
The title compound is a binuclear complex (Fig. 1) formed by bis[3-methyl-5-(pyridin-2-yl)-1H-pyrazol-4-yl]selenide (Seredyuk et al., 2010a). Each CuII ion is surrounded by three O atoms and two N atoms in a coordination geometry best described as tetragonal pyramidal. For both CuII ions, the equatorial planes are formed by a chelating pyrazole-pyridine group [Cu—N = 1.961 (7)–2.015 (7) Å], a water molecule [Cu1—O8 = 1.966 (6), Cu2—O1 = 1.978 (6) Å] and a nitrate O atom [Cu1—O10 = 1.988 (6), Cu2—O5 = 1.979 (7) Å], whereas the apical positions are occupied by a water molecule for Cu1 [Cu1—O9 = 2.254 (7) Å] and by a nitrate O atom for Cu2 [Cu2—O2 = 2.345 (7) Å]. The organic selenide adopts a trans configuration with a C–Se–C angle equal to 97.9 (4)°. The C—N and C—C bond lengths in the pyridine rings are normal for 2-substituted pyridine derivatives (Fritsky et al., 2004; Kanderal et al., 2005; Moroz et al., 2010, 2012).
An uncoordinated nitrate anion balancing the charge of the complex molecule serves as a bridge to connect three complex molecules through O—H···O and N—H···O hydrogen bonds (Table 1). Also, numerous intermolecular hydrogen bonds are observed between the water molecules and nitrate anions. π–π stacking interactions between the pyridine rings [averaged centroid–centroid distance = 3.652 (5) Å] are also present (Fig. 2).