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In the title compound, [Cu(C15H22NO)2], the CuII cation lies on a centre of symmetry. The coordination geometry about the CuII ion is a parallelogram, formed by the N2O2 donor set of the two bidentate long alkane chain Schiff base imine-phenol ligands. The Cu-N and Cu-O distances are 2.009 (3) and 1.888 (3) Å, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101013154/ta1334sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101013154/ta1334Isup2.hkl
Contains datablock I

CCDC reference: 174807

Comment top

In enzyme systems, metal ions play an important role in terms of both structure and function. Hard cations are not only involved in the structural properties of proteins, but also show catalytic activity. Over the past few decades, metal-Schiff base complexes have been extensively investigated with regard to their function as model compounds for biological enzymes (Espinet et al., 1992; Giroud-Godquin & Maitlis, 1991). Some N,O-containing metal-Schiff base complexes possessing high catalytic activity show potential application in the fields of catalysis and medicine (Jacobsen et al., 1991; Schmidt et al., 1996). Copper-Schiff base complexes play an important role in both synthetic and structural research because they are useful stereochemical models in catalytic chemistry, with their preparative accessibility and structural variety (Garnovskii et al., 1993). Tetracoordinated copper-Schiff base complexes may form trans or cis planar or tetrahedral structures. A strictly planar or slightly distorted coordination is characteristic of transition metal complexes of CuII with a CuN2O2 coordination sphere (Elerman, Elmali, Kabak & Svoboda, 1998; Elerman, Elmali & Özbey, 1998; Elmali et al., 2000; Kabak et al., 1999). Often, the geometry of a trans-planar copper complex is a parallelogram. Here, we report the results of the reaction of CuII with a long alkane chain ligand, N-octylsalicylideneamine, which forms a monomeric copper-Schiff base complex, (I), in a trans-planar parallelogram coordination geometry with the CuII ion on a crystallographic centre of symmetry (Fig. 1). \sch

The bond lengths and angles around the CuII ion in (I) are in good agreement with the values found in other similar copper complexes (Akhtar & Drew, 1982; Labisbal et al., 1994) and in long alkane chain metal-Schiff base complexes (Asada et al., 2000). The Cu—N distances are longer than the Cu—O distances. No unusual bond lengths and angles are observed in the salen ligands of (I). Long alkane chain C—C bond distances are in the range 1.473 (7)–1.528 (9), phenyl C—C bond distances are in the range 1.371 (6)–1.415 (5), C—O 1.304 (4), C—N 1.470 (4) and CN 1.288 (5) Å. These values are within the expected ranges for related salen derivatives (Blake et al., 1995; Zamian et al., 1995).

The molecules of the title copper-Schiff base complex exist as monomers, with Cu···Cu separations of 6.804 Å, leading to no dimeric interaction (Fig. 2). The long alkane chain molecules are stacked in columns along the a axis, while no connections are formed between the chain ends of two adjacent copper complexes. The alkane chains are reasonably linear, but the entire molecule is not as planar as some other copper-Schiff base complexes (Elmali et al., 2000; Kabak et al., 1999). No overlap between the aromatic rings of two adjacent [Cu(C15H22NO)2] units is seen, which is in contrast with the cases of π-stacking of aromatic rings that have recently been reported by Amoroso et al. (1995) and Muñoz et al. (1998).

Experimental top

To a solution of salicylaldehyde (2.0 mmol) in boiling absolute ethanol (10 ml), n-octylamine (2.0 mmol) was added dropwise. After stirring for a few minutes, a solution containing [Cu(O2CCH3)2]·H2O (1.0 mmol) and CH3CO2Na·3H2O (1.5 mmol) in hot water (6 ml) was added slowly to the boiling mixture. During this addition, a large amount of brown powder precipitated. The reaction mixture was refluxed for half an hour and then cooled to room temperature. The crystalline precipitate was filtered off (yield 80%). Brown single crystals of (I) (m.p. 337 K) suitable for X-ray diffraction were grown by slow evaporation over a few weeks. The product was soluble in organic solvents, e.g. chloroform. IR (KBr), ν (CN): 1618 and 1597 cm-1.

Refinement top

All H atoms were placed at calculated positions and treated as riding, with C—H = 0.93–0.97 Å and Uiso(H) = 1.5Ueq(C) for methyl H and 1.2Ueq(C) for other H atoms. Are these the correct constraints?

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure and atom-labelling scheme of (I). Displacement ellipsoids are plotted at the 30% probability level and H atoms are drawn as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A perspective view of the unit cell of (I). H atoms have been omitted for clarity.
Bis(N-octylsalicylideneaminato-N,O)copper(II) top
Crystal data top
[Cu(C15H22NO)2]F(000) = 566
Mr = 528.21Dx = 1.167 Mg m3
Monoclinic, P21/cMelting point: 337 K
a = 16.571 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.742 (3) ÅCell parameters from 37 reflections
c = 9.500 (3) ŵ = 0.75 mm1
β = 101.507 (5)°T = 298 K
V = 1502.9 (7) Å3Block, brown
Z = 20.20 × 0.20 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector Query
diffractometer
2656 independent reflections
Radiation source: fine-focus sealed tube1414 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
ϕ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1918
Tmin = 0.864, Tmax = 0.896k = 1110
6066 measured reflectionsl = 611
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048 w = 1/[[σ2(Fo2) + (0.05P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.126(Δ/σ)max = 0.017
S = 1.03Δρmax = 0.27 e Å3
2656 reflectionsΔρmin = 0.23 e Å3
160 parameters
Crystal data top
[Cu(C15H22NO)2]V = 1502.9 (7) Å3
Mr = 528.21Z = 2
Monoclinic, P21/cMo Kα radiation
a = 16.571 (4) ŵ = 0.75 mm1
b = 9.742 (3) ÅT = 298 K
c = 9.500 (3) Å0.20 × 0.20 × 0.15 mm
β = 101.507 (5)°
Data collection top
Bruker SMART CCD area-detector Query
diffractometer
2656 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1414 reflections with I > 2σ(I)
Tmin = 0.864, Tmax = 0.896Rint = 0.056
6066 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0482 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.03Δρmax = 0.27 e Å3
2656 reflectionsΔρmin = 0.23 e Å3
160 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.00000.00001.00000.0526 (3)
O10.06756 (17)0.0048 (3)0.8149 (3)0.0677 (8)
N10.02423 (17)0.2014 (3)0.9901 (3)0.0498 (9)
C10.0908 (2)0.2654 (4)1.0952 (4)0.0558 (11)
H1A0.08740.23451.19090.067*
H1B0.08370.36431.09200.067*
C20.1746 (2)0.2301 (4)1.0658 (5)0.0658 (12)
H2A0.17660.25580.96790.079*
H2B0.18280.13161.07460.079*
C30.2437 (3)0.3021 (5)1.1678 (5)0.0805 (15)
H3A0.23040.39891.17080.097*
H3B0.24690.26521.26360.097*
C40.3257 (3)0.2881 (6)1.1284 (6)0.109 (2)
H4A0.32250.32721.03350.131*
H4B0.33790.19121.12230.131*
C50.3969 (3)0.3555 (7)1.2304 (7)0.149 (3)
H5A0.40220.31431.32480.179*
H5B0.38500.45231.23900.179*
C60.4783 (4)0.3402 (9)1.1796 (10)0.194 (4)
H6A0.48750.24411.16120.233*
H6B0.47510.39001.09020.233*
C70.5480 (5)0.3928 (11)1.2870 (11)0.241 (5)
H7A0.55410.34141.37590.289*
H7B0.54030.48901.30700.289*
C80.6224 (5)0.3735 (12)1.2191 (12)0.271 (6)
H8A0.66960.41531.27870.407*
H8B0.61230.41571.12590.407*
H8C0.63250.27721.20960.407*
C110.1042 (2)0.1097 (4)0.7441 (5)0.0562 (11)
C120.1667 (3)0.0867 (5)0.6226 (5)0.0708 (13)
H12A0.18120.00310.59540.085*
C130.2067 (3)0.1929 (5)0.5432 (5)0.0778 (14)
H13A0.24790.17370.46370.093*
C140.1870 (3)0.3280 (5)0.5793 (5)0.0738 (13)
H14A0.21490.39980.52610.089*
C150.1251 (3)0.3533 (4)0.6960 (5)0.0636 (12)
H15A0.11060.44370.72010.076*
C160.0832 (2)0.2479 (4)0.7797 (4)0.0495 (10)
C170.0182 (2)0.2828 (4)0.8968 (5)0.0528 (11)
H17A0.00490.37550.90710.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0644 (4)0.0447 (4)0.0471 (4)0.0031 (4)0.0075 (3)0.0023 (4)
O10.0948 (19)0.0436 (16)0.0562 (18)0.0009 (17)0.0054 (15)0.0035 (17)
N10.056 (2)0.048 (2)0.046 (2)0.0016 (15)0.0104 (18)0.0070 (17)
C10.071 (3)0.047 (2)0.048 (3)0.008 (2)0.007 (2)0.006 (2)
C20.063 (3)0.064 (3)0.069 (3)0.013 (2)0.010 (2)0.002 (2)
C30.068 (3)0.102 (4)0.068 (3)0.014 (3)0.005 (3)0.004 (3)
C40.066 (3)0.138 (5)0.120 (5)0.007 (3)0.010 (3)0.006 (4)
C50.081 (4)0.220 (9)0.134 (6)0.047 (5)0.007 (4)0.021 (5)
C60.075 (5)0.290 (11)0.210 (9)0.050 (6)0.011 (6)0.001 (8)
C70.121 (7)0.326 (15)0.282 (14)0.036 (8)0.057 (8)0.031 (11)
C80.136 (8)0.381 (18)0.291 (15)0.020 (9)0.028 (9)0.028 (11)
C110.062 (3)0.060 (3)0.045 (3)0.002 (2)0.009 (2)0.002 (2)
C120.085 (3)0.054 (3)0.065 (3)0.005 (3)0.003 (3)0.004 (2)
C130.078 (3)0.078 (4)0.068 (4)0.001 (3)0.007 (3)0.007 (3)
C140.081 (3)0.064 (3)0.074 (4)0.017 (3)0.008 (3)0.017 (3)
C150.074 (3)0.051 (3)0.065 (3)0.004 (2)0.013 (3)0.005 (2)
C160.058 (3)0.046 (2)0.046 (3)0.001 (2)0.015 (2)0.001 (2)
C170.061 (3)0.043 (2)0.059 (3)0.004 (2)0.021 (2)0.006 (2)
Geometric parameters (Å, º) top
Cu1—O11.888 (3)C2—H2A0.97
Cu1—N12.009 (3)C2—H2B0.97
O1—C111.304 (4)C3—H3A0.97
N1—C171.288 (5)C3—H3B0.97
N1—C11.470 (4)C4—H4A0.97
C1—C21.511 (5)C4—H4B0.97
C2—C31.516 (5)C5—H5A0.97
C3—C41.487 (6)C5—H5B0.97
C4—C51.518 (7)C6—H6A0.97
C5—C61.528 (9)C6—H6B0.97
C6—C71.473 (7)C7—H7A0.97
C7—C81.512 (8)C7—H7B0.97
C11—C121.406 (5)C8—H8A0.96
C11—C161.415 (5)C8—H8B0.96
C12—C131.371 (6)C8—H8C0.96
C13—C141.383 (6)C12—H12A0.93
C14—C151.374 (5)C13—H13A0.93
C15—C161.395 (5)C14—H14A0.93
C16—C171.426 (5)C15—H15A0.93
C1—H1A0.97C17—H17A0.93
C1—H1B0.97
O1i—Cu1—O1180.0C4—C3—H3B109
O1i—Cu1—N188.91 (13)H3A—C3—H3B108
O1—Cu1—N191.09 (13)C3—C4—H4A108
N1—Cu1—N1i180.0C3—C4—H4B108
C11—O1—Cu1128.9 (3)C5—C4—H4A108
C17—N1—C1116.0 (3)C5—C4—H4B108
C17—N1—Cu1123.1 (3)H4A—C4—H4B107
C1—N1—Cu1120.8 (2)C4—C5—H5A109
N1—C1—C2111.8 (3)C4—C5—H5B109
C1—C2—C3112.4 (4)C6—C5—H5A109
C4—C3—C2114.1 (4)C6—C5—H5B109
C3—C4—C5115.6 (5)H5A—C5—H5B108
C4—C5—C6112.2 (6)C5—C6—H6A109
C7—C6—C5111.5 (7)C5—C6—H6B109
C6—C7—C8104.8 (7)C7—C6—H6A109
O1—C11—C12119.3 (4)C7—C6—H6B109
O1—C11—C16123.8 (4)H6A—C6—H6B108
C12—C11—C16117.0 (4)C6—C7—H7A111
C13—C12—C11121.9 (4)C6—C7—H7B111
C12—C13—C14121.1 (4)C8—C7—H7A111
C15—C14—C13118.1 (4)C8—C7—H7B111
C14—C15—C16122.3 (4)H7A—C7—H7B109
C15—C16—C11119.5 (4)C7—C8—H8A110
C15—C16—C17118.8 (4)C7—C8—H8B110
C11—C16—C17121.6 (4)C7—C8—H8C110
N1—C17—C16127.9 (4)H8A—C8—H8B110
N1—C1—H1A109H8B—C8—H8C110
N1—C1—H1B109H8C—C8—H8A110
C2—C1—H1A109C11—C12—H12A119
C2—C1—H1B109C13—C12—H12A119
H1A—C1—H1B108C12—C13—H13A119
C1—C2—H2A109C14—C13—H13A119
C1—C2—H2B109C13—C14—H14A121
C3—C2—H2A109C15—C14—H14A121
C3—C2—H2B109C14—C15—H15A119
H2A—C2—H2B108C16—C15—H15A119
C2—C3—H3A109C16—C17—H17A116
C2—C3—H3B109N1—C17—H17A116
C4—C3—H3A109
Symmetry code: (i) x, y, z+2.

Experimental details

Crystal data
Chemical formula[Cu(C15H22NO)2]
Mr528.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)16.571 (4), 9.742 (3), 9.500 (3)
β (°) 101.507 (5)
V3)1502.9 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.75
Crystal size (mm)0.20 × 0.20 × 0.15
Data collection
DiffractometerBruker SMART CCD area-detector Query
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.864, 0.896
No. of measured, independent and
observed [I > 2σ(I)] reflections
6066, 2656, 1414
Rint0.056
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.126, 1.03
No. of reflections2656
No. of parameters160
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.23

Computer programs: SMART (Bruker, 2001), SMART, SHELXTL (Bruker, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
Cu1—O11.888 (3)Cu1—N12.009 (3)
O1i—Cu1—N188.91 (13)O1—Cu1—N191.09 (13)
Symmetry code: (i) x, y, z+2.
 

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