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Acta Cryst. (2007). E63, m2358    [ doi:10.1107/S1600536807039669 ]

(2,2'-Bipyridine-[kappa]2N,N')(1-formyl-2-naphtholato-[kappa]2O,O')(nitrato-[kappa]O)copper(II)

B.-R. Lian, J.-X. Li, Y.-M. Jiang and B.-L. Liang

Abstract top

In the title mononuclear complex, [Cu(C11H7O2)(NO3)(C10H8N2)], the CuII atom is five-coordinated in a distorted square-pyramidal environment by two N atoms of 2,2'-bipyridine, two O atoms of 1-formyl-2-naphtholate and a nitrate O atom. Molecules are stacked by [pi]-[pi] interactions [the dihedral angle, interplanar average distance and ring-centroid separation involved in stacking are 0.000 (1), 3.3504 (2) and 4.0800 (7) Å for stronger interactions, and 2.505 (1), 3.5373 (2) and 4.2048 (9) Å for weaker interactions] into a one-dimensional structure.

Comment top

In the previously published papers, the crystal structures of 2-hydroxy-1-naphthaldehyde (Maniukiewicz & Bukowska-Strzyzewska, 1992) and its three copper(II) complexes (Yu et al., 2006; Xiu-Jian et al., 2005; Elmali & Elerman, 2002) have been determined. In this paper, we report a new compound containing naphthaldehyde as a ligand (Fig.1). The CuII atom is five-coordinated by two N atoms of bipy and two O atoms of naph in the equatorial plane with an axial nitrate O—Cu bond to form square-pyramidal coordination geometry (Table 1). The Cu atom is shifted from from the least-squares plane N1/N2/O2/O1 by 0.2103 (3)Å towards O3. The presented structure comprises the same cation as [Cu(C10H8N2)(C11H7O2)(ClO4)] (Elmali & Elerman, 2002) but anions are different: nitrate and perchlorate. In the crystal structure of (I), there are two kinds of π-π stacking interactions: strong one between naphthalene rings (symmetry codes: −x + 1, y − 1/2, −z + 1/2; x, −y + 3/2, z + 1/2) and the weak one between naphthalene ring and pyridine ring (symmetry codes: −x + 1, y − 1/2, −z + 1/2; x, y − 1/2, z + 1/2). The dihedral angle, interplanar average distance and ring-centroid separation distance are: 0.000 (1)°, 3.3504 (2) Å, 4.0800 (7)Å for the former ones and 2.505 (1)°, 3.5373 (2) Å, 4.2048 (9)Å for the latter ones, respectively. The title molecules are connected into dimers through the first kind of stacking and further linked into a one-dimensional skeleton via the second π-π stacking along c axis (Fig. 2).

Related literature top

For related literature, see: Elmali & Elerman (2002); Maniukiewicz & Bukowska-Strzyzewska (1992); Xiu-Jian et al. (2005); Yu et al. (2006).

Experimental top

A 10 ml me thanol solution of Cu(NO3)2·3H2O (0.242 g,1 mmol) was dropped into 10 ml me thanol solution of 2, 2'-bipyridine(0.156 g,1 mmol) and 2-hydroxy-1-naphthaldehyde (0.16 g,1 mmol) to be stirred for 5 h at 323 K. By an evaporation of the filtrate for about 10 days green block-shaped crystals were obtained. Analysis, found (%): C, 55.60; H, 3.35; N, 9.21. C21H15CuN3O5 required (%):C, 55.64; H, 3.31; N, 9.27.

Refinement top

H atoms were positioned geometrically with C—H distance of 0.93 Å, and treated as riding atoms, with Uiso(H)=1.2Ueq(C).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with the atom-numbering scheme and displacement parameters scaled at the 30% probability.
[Figure 2] Fig. 2. Packing of (I) showing the one-dimensional structure in the ab plane, linked π-π stacking (dashed lines). H atoms have been omitted.
(2,2'-Bipyridine-κ2N,N')(1-formyl-2-naphtholato-κ2O,O')(nitrato-\ κO)copper(II) top
Crystal data top
[Cu(C11H7O2)(NO3)(C10H8N2)]F000 = 924
Mr = 452.90Dx = 1.618 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 38 reflections
a = 12.428 (3) Åθ = 4.6–15.2º
b = 9.167 (2) ŵ = 1.22 mm−1
c = 17.245 (6) ÅT = 296 (2) K
β = 108.85 (1)ºBlock, green
V = 1859.3 (9) Å30.56 × 0.48 × 0.36 mm
Z = 4
Data collection top
Siemens P4
diffractometer		Rint = 0.017
Radiation source: normal-focus sealed tubeθmax = 25.0º
Monochromator: graphiteθmin = 1.7º
T = 296(2) Kh = 0→14
ω scansk = 0→10
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)		l = −20→19
Tmin = 0.767, Tmax = 0.9853 standard reflections
3797 measured reflections every 97 reflections
3261 independent reflections intensity decay: 1.4%
2552 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034  w = 1/[σ2(Fo2) + (0.0535P)2 + 0.0639P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.093(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.36 e Å−3
3261 reflectionsΔρmin = −0.39 e Å−3
272 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00014 (4)
Secondary atom site location: difference Fourier map
Crystal data top
[Cu(C11H7O2)(NO3)(C10H8N2)]V = 1859.3 (9) Å3
Mr = 452.90Z = 4
Monoclinic, P21/cMo Kα
a = 12.428 (3) ŵ = 1.22 mm−1
b = 9.167 (2) ÅT = 296 (2) K
c = 17.245 (6) Å0.56 × 0.48 × 0.36 mm
β = 108.85 (1)º
Data collection top
Siemens P4
diffractometer		2552 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)		Rint = 0.017
Tmin = 0.767, Tmax = 0.9853 standard reflections
3797 measured reflections every 97 reflections
3261 independent reflections intensity decay: 1.4%
Refinement top
R[F2 > 2σ(F2)] = 0.034272 parameters
wR(F2) = 0.093H-atom parameters constrained
S = 1.05Δρmax = 0.36 e Å−3
3261 reflectionsΔρmin = −0.39 e Å−3
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
Cu0.69710 (3)0.56548 (4)0.01255 (2)0.04165 (14)
O10.57130 (15)0.6902 (2)−0.03875 (11)0.0465 (5)
O20.64002 (17)0.5217 (2)0.10181 (12)0.0488 (5)
O30.8122 (2)0.7602 (3)0.05872 (16)0.0885 (9)
O40.8697 (3)0.6778 (3)0.18001 (17)0.1045 (10)
O50.9546 (2)0.8586 (3)0.14903 (16)0.0751 (7)
N10.73773 (19)0.5505 (3)−0.08999 (14)0.0424 (5)
N20.81823 (18)0.4139 (2)0.04854 (14)0.0412 (5)
N30.8786 (2)0.7689 (3)0.12895 (18)0.0549 (7)
C10.5021 (2)0.7470 (3)−0.00535 (17)0.0408 (6)
C20.4219 (2)0.8518 (3)−0.05254 (18)0.0473 (7)
H20.41950.8722−0.10590.057*
C30.3493 (2)0.9216 (3)−0.02088 (19)0.0488 (7)
H30.29820.9886−0.05340.059*
C40.3487 (2)0.8958 (3)0.06057 (18)0.0448 (7)
C50.2758 (3)0.9761 (4)0.0928 (2)0.0590 (9)
H50.22811.04690.06090.071*
C60.2749 (3)0.9502 (4)0.1705 (2)0.0664 (10)
H60.22721.00380.19150.080*
C70.3455 (3)0.8437 (4)0.2182 (2)0.0573 (8)
H70.34380.82520.27080.069*
C80.4175 (2)0.7658 (3)0.18808 (18)0.0492 (7)
H80.46470.69590.22120.059*
C90.4220 (2)0.7884 (3)0.10894 (17)0.0413 (6)
C100.4987 (2)0.7101 (3)0.07414 (17)0.0390 (6)
C110.5631 (2)0.5932 (3)0.11747 (18)0.0445 (7)
H110.54670.56450.16420.053*
C120.6931 (3)0.6285 (4)−0.15859 (19)0.0550 (8)
H120.63640.6959−0.16060.066*
C130.7278 (3)0.6129 (4)−0.2256 (2)0.0678 (10)
H130.69470.6684−0.27240.081*
C140.8112 (3)0.5152 (4)−0.2232 (2)0.0660 (10)
H140.83620.5042−0.26820.079*
C150.8582 (3)0.4327 (3)−0.1540 (2)0.0563 (8)
H150.91470.3647−0.15180.068*
C160.8204 (2)0.4523 (3)−0.08780 (17)0.0401 (6)
C170.8641 (2)0.3727 (3)−0.00911 (17)0.0418 (6)
C180.9466 (2)0.2650 (3)0.0066 (2)0.0554 (8)
H180.97690.2364−0.03380.066*
C190.9828 (3)0.2011 (4)0.0830 (2)0.0625 (9)
H191.03780.12820.09450.075*
C200.9380 (3)0.2448 (4)0.1418 (2)0.0585 (8)
H200.96260.20310.19370.070*
C210.8559 (2)0.3514 (3)0.12283 (18)0.0506 (7)
H210.82530.38140.16290.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.0377 (2)0.0452 (2)0.0434 (2)0.00772 (16)0.01494 (15)0.00289 (17)
O10.0394 (10)0.0579 (12)0.0442 (11)0.0120 (9)0.0163 (9)0.0046 (10)
O20.0461 (11)0.0510 (12)0.0537 (12)0.0101 (10)0.0222 (10)0.0094 (10)
O30.0918 (19)0.0642 (16)0.0767 (18)−0.0083 (15)−0.0184 (15)0.0074 (14)
O40.133 (3)0.104 (2)0.0666 (18)−0.047 (2)0.0194 (18)−0.0145 (17)
O50.0671 (15)0.0790 (17)0.0836 (17)−0.0268 (14)0.0306 (14)−0.0271 (15)
N10.0400 (12)0.0448 (13)0.0423 (13)0.0051 (11)0.0131 (11)0.0022 (11)
N20.0367 (12)0.0435 (14)0.0430 (13)0.0038 (10)0.0122 (10)0.0043 (11)
N30.0523 (16)0.0560 (17)0.0592 (18)0.0004 (14)0.0217 (14)−0.0173 (15)
C10.0320 (13)0.0392 (14)0.0479 (16)−0.0014 (12)0.0084 (12)−0.0052 (13)
C20.0453 (16)0.0486 (17)0.0450 (17)0.0040 (14)0.0104 (14)−0.0001 (14)
C30.0379 (15)0.0451 (17)0.0575 (19)0.0083 (13)0.0072 (14)0.0026 (15)
C40.0382 (15)0.0439 (16)0.0508 (18)0.0013 (12)0.0122 (13)−0.0083 (13)
C50.0515 (19)0.058 (2)0.067 (2)0.0163 (15)0.0185 (17)−0.0033 (17)
C60.061 (2)0.070 (2)0.078 (2)0.0111 (18)0.0358 (19)−0.013 (2)
C70.0594 (19)0.064 (2)0.0532 (19)−0.0018 (17)0.0253 (16)−0.0111 (17)
C80.0470 (17)0.0502 (18)0.0515 (18)0.0001 (14)0.0173 (15)−0.0072 (15)
C90.0349 (14)0.0403 (15)0.0474 (16)−0.0061 (12)0.0114 (12)−0.0090 (13)
C100.0331 (13)0.0406 (15)0.0434 (15)−0.0020 (12)0.0127 (12)−0.0040 (12)
C110.0423 (16)0.0475 (17)0.0467 (17)0.0011 (13)0.0185 (13)0.0009 (13)
C120.0528 (18)0.0598 (19)0.0525 (19)0.0175 (16)0.0172 (15)0.0110 (16)
C130.073 (2)0.081 (2)0.055 (2)0.024 (2)0.0279 (18)0.0241 (18)
C140.071 (2)0.080 (2)0.059 (2)0.015 (2)0.0382 (19)0.0156 (19)
C150.0525 (18)0.062 (2)0.062 (2)0.0147 (16)0.0302 (16)0.0096 (17)
C160.0323 (13)0.0416 (15)0.0449 (16)0.0011 (12)0.0103 (12)0.0019 (13)
C170.0328 (14)0.0429 (15)0.0497 (17)−0.0019 (12)0.0132 (13)0.0026 (13)
C180.0474 (17)0.0566 (19)0.067 (2)0.0157 (15)0.0246 (16)0.0078 (17)
C190.0501 (19)0.063 (2)0.074 (2)0.0231 (16)0.0193 (17)0.0189 (18)
C200.0518 (18)0.063 (2)0.0549 (19)0.0085 (17)0.0093 (16)0.0190 (17)
C210.0472 (17)0.0568 (19)0.0474 (18)0.0032 (15)0.0149 (14)0.0057 (15)
Geometric parameters (Å, °) top
Cu—O11.9082 (18)C6—H60.9300
Cu—O21.934 (2)C7—C81.372 (4)
Cu—N11.994 (2)C7—H70.9300
Cu—N21.995 (2)C8—C91.399 (4)
Cu—O32.265 (3)C8—H80.9300
O1—C11.289 (3)C9—C101.468 (4)
O2—C111.259 (3)C10—C111.400 (4)
O3—N31.228 (3)C11—H110.9300
O4—N31.244 (4)C12—C131.365 (4)
O5—N31.215 (3)C12—H120.9300
N1—C121.339 (4)C13—C141.360 (4)
N1—C161.357 (3)C13—H130.9300
N2—C211.342 (4)C14—C151.374 (4)
N2—C171.350 (3)C14—H140.9300
C1—C101.426 (4)C15—C161.379 (4)
C1—C21.434 (4)C15—H150.9300
C2—C31.356 (4)C16—C171.481 (4)
C2—H20.9300C17—C181.385 (4)
C3—C41.427 (4)C18—C191.378 (4)
C3—H30.9300C18—H180.9300
C4—C51.414 (4)C19—C201.365 (4)
C4—C91.415 (4)C19—H190.9300
C5—C61.363 (5)C20—C211.375 (4)
C5—H50.9300C20—H200.9300
C6—C71.390 (5)C21—H210.9300
O1—Cu—O292.12 (8)C7—C8—C9121.9 (3)
O1—Cu—N191.97 (9)C7—C8—H8119.1
O2—Cu—N1162.68 (9)C9—C8—H8119.1
O1—Cu—N2169.98 (9)C8—C9—C4117.2 (3)
O2—Cu—N292.40 (9)C8—C9—C10124.2 (3)
N1—Cu—N281.15 (9)C4—C9—C10118.6 (3)
O1—Cu—O391.16 (9)C11—C10—C1120.3 (2)
O2—Cu—O3103.65 (10)C11—C10—C9119.4 (3)
N1—Cu—O393.08 (10)C1—C10—C9120.2 (2)
N2—Cu—O396.45 (10)O2—C11—C10128.8 (3)
C1—O1—Cu126.84 (18)O2—C11—H11115.6
C11—O2—Cu124.22 (19)C10—C11—H11115.6
N3—O3—Cu123.0 (2)N1—C12—C13122.6 (3)
C12—N1—C16118.2 (2)N1—C12—H12118.7
C12—N1—Cu126.5 (2)C13—C12—H12118.7
C16—N1—Cu115.28 (18)C14—C13—C12119.3 (3)
C21—N2—C17119.0 (2)C14—C13—H13120.4
C21—N2—Cu126.1 (2)C12—C13—H13120.4
C17—N2—Cu114.94 (18)C13—C14—C15119.6 (3)
O5—N3—O3122.5 (3)C13—C14—H14120.2
O5—N3—O4119.4 (3)C15—C14—H14120.2
O3—N3—O4118.0 (3)C14—C15—C16119.0 (3)
O1—C1—C10124.4 (2)C14—C15—H15120.5
O1—C1—C2117.3 (3)C16—C15—H15120.5
C10—C1—C2118.2 (2)N1—C16—C15121.4 (3)
C3—C2—C1121.3 (3)N1—C16—C17113.8 (2)
C3—C2—H2119.4C15—C16—C17124.9 (3)
C1—C2—H2119.4N2—C17—C18121.2 (3)
C2—C3—C4122.3 (3)N2—C17—C16114.8 (2)
C2—C3—H3118.9C18—C17—C16124.0 (3)
C4—C3—H3118.9C19—C18—C17118.8 (3)
C5—C4—C9120.2 (3)C19—C18—H18120.6
C5—C4—C3120.6 (3)C17—C18—H18120.6
C9—C4—C3119.2 (3)C20—C19—C18120.0 (3)
C6—C5—C4120.4 (3)C20—C19—H19120.0
C6—C5—H5119.8C18—C19—H19120.0
C4—C5—H5119.8C19—C20—C21118.8 (3)
C5—C6—C7120.0 (3)C19—C20—H20120.6
C5—C6—H6120.0C21—C20—H20120.6
C7—C6—H6120.0N2—C21—C20122.2 (3)
C8—C7—C6120.4 (3)N2—C21—H21118.9
C8—C7—H7119.8C20—C21—H21118.9
C6—C7—H7119.8
O2—Cu—O1—C117.3 (2)C7—C8—C9—C10178.9 (3)
N1—Cu—O1—C1−179.5 (2)C5—C4—C9—C80.6 (4)
N2—Cu—O1—C1134.1 (4)C3—C4—C9—C8−179.3 (3)
O3—Cu—O1—C1−86.4 (2)C5—C4—C9—C10−178.3 (3)
O1—Cu—O2—C11−14.7 (2)C3—C4—C9—C101.7 (4)
N1—Cu—O2—C11−118.3 (3)O1—C1—C10—C11−8.3 (4)
N2—Cu—O2—C11174.2 (2)C2—C1—C10—C11170.3 (2)
O3—Cu—O2—C1177.0 (2)O1—C1—C10—C9175.7 (2)
O1—Cu—O3—N3135.3 (3)C2—C1—C10—C9−5.7 (4)
O2—Cu—O3—N342.8 (3)C8—C9—C10—C117.8 (4)
N1—Cu—O3—N3−132.7 (3)C4—C9—C10—C11−173.3 (2)
N2—Cu—O3—N3−51.3 (3)C8—C9—C10—C1−176.1 (3)
O1—Cu—N1—C129.0 (3)C4—C9—C10—C12.7 (4)
O2—Cu—N1—C12112.6 (3)Cu—O2—C11—C103.8 (4)
N2—Cu—N1—C12−178.3 (3)C1—C10—C11—O211.0 (4)
O3—Cu—N1—C12−82.3 (3)C9—C10—C11—O2−173.0 (3)
O1—Cu—N1—C16−172.13 (19)C16—N1—C12—C13−0.1 (5)
O2—Cu—N1—C16−68.5 (4)Cu—N1—C12—C13178.7 (3)
N2—Cu—N1—C160.55 (19)N1—C12—C13—C14−0.3 (6)
O3—Cu—N1—C1696.6 (2)C12—C13—C14—C150.7 (6)
O1—Cu—N2—C21−134.5 (4)C13—C14—C15—C16−0.7 (5)
O2—Cu—N2—C21−17.7 (2)C12—N1—C16—C150.1 (4)
N1—Cu—N2—C21178.5 (2)Cu—N1—C16—C15−178.8 (2)
O3—Cu—N2—C2186.3 (2)C12—N1—C16—C17179.7 (3)
O1—Cu—N2—C1745.2 (6)Cu—N1—C16—C170.7 (3)
O2—Cu—N2—C17161.98 (19)C14—C15—C16—N10.3 (5)
N1—Cu—N2—C17−1.86 (18)C14—C15—C16—C17−179.2 (3)
O3—Cu—N2—C17−94.0 (2)C21—N2—C17—C181.8 (4)
Cu—O3—N3—O5165.6 (2)Cu—N2—C17—C18−177.9 (2)
Cu—O3—N3—O4−11.3 (4)C21—N2—C17—C16−177.5 (2)
Cu—O1—C1—C10−8.8 (4)Cu—N2—C17—C162.8 (3)
Cu—O1—C1—C2172.60 (18)N1—C16—C17—N2−2.3 (3)
O1—C1—C2—C3−177.1 (3)C15—C16—C17—N2177.2 (3)
C10—C1—C2—C34.3 (4)N1—C16—C17—C18178.4 (3)
C1—C2—C3—C40.2 (4)C15—C16—C17—C18−2.1 (5)
C2—C3—C4—C5176.8 (3)N2—C17—C18—C19−0.9 (5)
C2—C3—C4—C9−3.3 (4)C16—C17—C18—C19178.3 (3)
C9—C4—C5—C6−0.4 (5)C17—C18—C19—C20−0.4 (5)
C3—C4—C5—C6179.5 (3)C18—C19—C20—C210.8 (5)
C4—C5—C6—C7−0.5 (5)C17—N2—C21—C20−1.3 (4)
C5—C6—C7—C81.1 (5)Cu—N2—C21—C20178.3 (2)
C6—C7—C8—C9−0.8 (5)C19—C20—C21—N20.1 (5)
C7—C8—C9—C40.0 (4)
Table 1
Selected geometric parameters (Å, °) top
Cu—O11.9082 (18)Cu—N21.995 (2)
Cu—O21.934 (2)Cu—O32.265 (3)
Cu—N11.994 (2)
O1—Cu—O292.12 (8)N1—Cu—N281.15 (9)
O1—Cu—N191.97 (9)O1—Cu—O391.16 (9)
O1—Cu—N2169.98 (9)N2—Cu—O396.45 (10)
O2—Cu—N292.40 (9)
Acknowledgements top

This work was supported by the Guangxi Science Foundation of the Guangxi Chuang Autonomous Region of the People's Republic of China (grant No. 0731053).

references
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