Bis{(E)-2-[1-(eth-oxy-imino)-eth-yl]-1-naphtho-lato-κN,O}copper(II).

In the title complex, [Cu(C(14)H(14)NO(2))(2)], the discrete complex mol-ecules have crystallographic inversion symmetry. The slightly distorted square-planar coordination sphere of the Cu(II) atom comprises two phenolate O atoms and two oxime N atoms from two bidentate-chelate 2-[1-(eth-oxy-imino)-eth-yl]-1-naphtho-late O-ethyl oxime (L(-)) ligands [Cu-O = 1.8919 (17) Å and Cu-N = 1.988 (2) Å]. The two naphthalene ring systems in the mol-ecule are parallel, with a perpendicular inter-planar spacing of 1.473 (2) Å, while each complex unit forms links to four other mol-ecules via inter-molecular methyl C-H⋯π inter-actions, giving an infinite cross-linked layered supra-molecular structure.

Related literature

For background to oximes, see: Chaudhuri (2003 ▶); Dong et al. (2007 ▶, 2008 ▶). For related structures, see: Zhao et al. (2009 ▶); Dong, Zhao et al. (2009 ▶). For the synthesis of the title complex, see: Dong, Tong et al. (2009 ▶). For the biological activity of copper(II) complexes, see: Karmaka et al. (2007 ▶).

Experimental

Crystal data

[Cu(C14H14NO2)2]

M = 520.06

Monoclinic,

a = 11.317 (1) Å

b = 7.1092 (8) Å

c = 15.171 (2) Å

β = 96.317 (1)°

V = 1213.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.94 mm−1

T = 298 K

0.17 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.857, T max = 0.912

6095 measured reflections

2130 independent reflections

1490 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.081

S = 1.01

2130 reflections

162 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047574/zs2078sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047574/zs2078Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C14H14NO2)2]	F(000) = 542
Mr = 520.06	Dx = 1.424 Mg m−3
Monoclinic, P21/c	Melting point = 315–316 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.317 (1) Å	Cell parameters from 1730 reflections
b = 7.1092 (8) Å	θ = 2.7–25.5°
c = 15.171 (2) Å	µ = 0.94 mm−1
β = 96.317 (1)°	T = 298 K
V = 1213.1 (2) Å3	Block-like, brown
Z = 2	0.17 × 0.15 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	2130 independent reflections
Radiation source: fine-focus sealed tube	1490 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→13
Tmin = 0.857, Tmax = 0.912	k = −8→8
6095 measured reflections	l = −18→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0342P)2] where P = (Fo2 + 2Fc2)/3
2130 reflections	(Δ/σ)max < 0.001
162 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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
Cu1	0.5000	0.5000	0.5000	0.03833 (17)
N1	0.63479 (18)	0.5872 (3)	0.58534 (14)	0.0381 (6)
O1	0.75134 (16)	0.6050 (3)	0.55763 (12)	0.0514 (6)
O2	0.39686 (15)	0.6209 (3)	0.57215 (12)	0.0462 (5)
C1	0.7502 (3)	0.7498 (5)	0.49108 (19)	0.0576 (9)
H1A	0.7131	0.8627	0.5111	0.069*
H1B	0.7052	0.7081	0.4365	0.069*
C2	0.8761 (3)	0.7901 (6)	0.4756 (2)	0.0789 (12)
H2A	0.9179	0.8426	0.5284	0.118*
H2B	0.8770	0.8781	0.4277	0.118*
H2C	0.9141	0.6754	0.4608	0.118*
C3	0.7501 (2)	0.6552 (4)	0.72791 (18)	0.0479 (8)
H3A	0.7842	0.5401	0.7521	0.072*
H3B	0.7344	0.7376	0.7754	0.072*
H3C	0.8047	0.7149	0.6926	0.072*
C4	0.6356 (2)	0.6131 (4)	0.67096 (17)	0.0359 (7)
C5	0.4124 (2)	0.6230 (4)	0.65963 (17)	0.0371 (7)
C6	0.5233 (2)	0.6069 (4)	0.71082 (17)	0.0343 (6)
C7	0.5266 (3)	0.5992 (4)	0.80539 (17)	0.0416 (7)
H7	0.5994	0.5806	0.8391	0.050*
C8	0.4279 (3)	0.6180 (4)	0.84775 (19)	0.0468 (8)
H8	0.4345	0.6127	0.9093	0.056*
C9	0.3147 (3)	0.6458 (4)	0.79925 (19)	0.0436 (7)
C10	0.3059 (2)	0.6458 (4)	0.70468 (18)	0.0397 (7)
C11	0.1938 (3)	0.6651 (4)	0.6560 (2)	0.0525 (9)
H11	0.1878	0.6652	0.5944	0.063*
C12	0.0930 (3)	0.6838 (5)	0.6976 (2)	0.0690 (11)
H12	0.0193	0.6941	0.6642	0.083*
C13	0.1009 (3)	0.6873 (5)	0.7907 (3)	0.0701 (11)
H13	0.0324	0.7016	0.8188	0.084*
C14	0.2079 (3)	0.6699 (4)	0.8396 (2)	0.0597 (9)
H14	0.2117	0.6738	0.9012	0.072*

	U11	U22	U33	U12	U13	U23
Cu1	0.0347 (3)	0.0528 (3)	0.0283 (3)	−0.0002 (3)	0.00671 (19)	−0.0033 (3)
N1	0.0276 (12)	0.0548 (15)	0.0336 (13)	0.0001 (11)	0.0112 (10)	0.0019 (11)
O1	0.0376 (11)	0.0795 (16)	0.0378 (12)	−0.0024 (11)	0.0064 (9)	0.0103 (11)
O2	0.0370 (11)	0.0722 (15)	0.0297 (11)	0.0050 (10)	0.0047 (9)	−0.0089 (10)
C1	0.057 (2)	0.068 (2)	0.049 (2)	−0.0095 (18)	0.0098 (16)	0.0089 (18)
C2	0.063 (2)	0.115 (3)	0.062 (2)	−0.026 (2)	0.0169 (18)	0.010 (2)
C3	0.0407 (17)	0.061 (2)	0.0410 (17)	−0.0053 (15)	0.0005 (14)	−0.0029 (15)
C4	0.0426 (17)	0.0317 (17)	0.0331 (16)	−0.0011 (13)	0.0028 (13)	0.0029 (13)
C5	0.0412 (17)	0.0341 (17)	0.0373 (17)	−0.0041 (13)	0.0106 (13)	−0.0056 (13)
C6	0.0407 (16)	0.0330 (16)	0.0304 (15)	−0.0024 (13)	0.0089 (13)	−0.0023 (13)
C7	0.0496 (18)	0.0411 (18)	0.0343 (16)	−0.0036 (15)	0.0058 (14)	−0.0022 (14)
C8	0.067 (2)	0.044 (2)	0.0312 (16)	−0.0051 (16)	0.0149 (15)	−0.0029 (14)
C9	0.0541 (19)	0.0359 (18)	0.0441 (18)	−0.0057 (14)	0.0203 (15)	−0.0037 (14)
C10	0.0414 (17)	0.0389 (18)	0.0407 (17)	−0.0043 (13)	0.0133 (14)	−0.0066 (13)
C11	0.0437 (19)	0.070 (2)	0.0452 (19)	0.0008 (16)	0.0136 (15)	−0.0055 (16)
C12	0.047 (2)	0.095 (3)	0.067 (3)	0.0030 (19)	0.0158 (18)	−0.005 (2)
C13	0.052 (2)	0.088 (3)	0.076 (3)	0.001 (2)	0.034 (2)	−0.003 (2)
C14	0.077 (2)	0.058 (2)	0.050 (2)	−0.0055 (19)	0.035 (2)	−0.0022 (17)

Cu1—O2	1.8919 (17)	C4—C6	1.467 (3)
Cu1—O2i	1.8919 (17)	C5—C6	1.406 (4)
Cu1—N1	1.988 (2)	C5—C10	1.459 (3)
Cu1—N1i	1.988 (2)	C6—C7	1.432 (3)
N1—C4	1.311 (3)	C7—C8	1.355 (3)
N1—O1	1.433 (2)	C7—H7	0.9300
O1—C1	1.441 (3)	C8—C9	1.419 (4)
O2—C5	1.320 (3)	C8—H8	0.9300
C1—C2	1.497 (4)	C9—C14	1.425 (4)
C1—H1A	0.9700	C9—C10	1.427 (4)
C1—H1B	0.9700	C10—C11	1.403 (4)
C2—H2A	0.9600	C11—C12	1.369 (4)
C2—H2B	0.9600	C11—H11	0.9300
C2—H2C	0.9600	C12—C13	1.406 (4)
C3—C4	1.506 (3)	C12—H12	0.9300
C3—H3A	0.9600	C13—C14	1.355 (4)
C3—H3B	0.9600	C13—H13	0.9300
C3—H3C	0.9600	C14—H14	0.9300
O2—Cu1—O2i	180.00 (8)	C6—C4—C3	119.9 (2)
O2—Cu1—N1	87.68 (8)	O2—C5—C6	124.6 (2)
O2i—Cu1—N1	92.32 (8)	O2—C5—C10	116.5 (2)
O2—Cu1—N1i	92.32 (8)	C6—C5—C10	118.9 (2)
O2i—Cu1—N1i	87.68 (8)	C5—C6—C7	118.7 (2)
N1—Cu1—N1i	180.0	C5—C6—C4	122.1 (2)
C4—N1—O1	111.8 (2)	C7—C6—C4	119.1 (2)
C4—N1—Cu1	127.60 (18)	C8—C7—C6	122.6 (3)
O1—N1—Cu1	120.09 (14)	C8—C7—H7	118.7
N1—O1—C1	109.3 (2)	C6—C7—H7	118.7
C5—O2—Cu1	124.36 (17)	C7—C8—C9	120.8 (3)
O1—C1—C2	108.1 (3)	C7—C8—H8	119.6
O1—C1—H1A	110.1	C9—C8—H8	119.6
C2—C1—H1A	110.1	C8—C9—C14	123.7 (3)
O1—C1—H1B	110.1	C8—C9—C10	118.7 (2)
C2—C1—H1B	110.1	C14—C9—C10	117.6 (3)
H1A—C1—H1B	108.4	C11—C10—C9	119.2 (3)
C1—C2—H2A	109.5	C11—C10—C5	120.7 (2)
C1—C2—H2B	109.5	C9—C10—C5	120.1 (3)
H2A—C2—H2B	109.5	C12—C11—C10	121.2 (3)
C1—C2—H2C	109.5	C12—C11—H11	119.4
H2A—C2—H2C	109.5	C10—C11—H11	119.4
H2B—C2—H2C	109.5	C11—C12—C13	120.1 (3)
C4—C3—H3A	109.5	C11—C12—H12	120.0
C4—C3—H3B	109.5	C13—C12—H12	120.0
H3A—C3—H3B	109.5	C14—C13—C12	120.2 (3)
C4—C3—H3C	109.5	C14—C13—H13	119.9
H3A—C3—H3C	109.5	C12—C13—H13	119.9
H3B—C3—H3C	109.5	C13—C14—C9	121.7 (3)
N1—C4—C6	119.5 (2)	C13—C14—H14	119.2
N1—C4—C3	120.5 (2)	C9—C14—H14	119.2
O2—Cu1—N1—C4	31.5 (2)	C3—C4—C6—C7	−13.8 (4)
O2i—Cu1—N1—C4	−148.5 (2)	C5—C6—C7—C8	−4.0 (4)
O2—Cu1—N1—O1	−157.06 (19)	C4—C6—C7—C8	171.1 (3)
O2i—Cu1—N1—O1	22.94 (19)	C6—C7—C8—C9	0.3 (5)
C4—N1—O1—C1	−122.4 (3)	C7—C8—C9—C14	−178.8 (3)
Cu1—N1—O1—C1	64.9 (3)	C7—C8—C9—C10	2.6 (4)
N1—Cu1—O2—C5	−38.7 (2)	C8—C9—C10—C11	177.3 (3)
N1i—Cu1—O2—C5	141.3 (2)	C14—C9—C10—C11	−1.4 (4)
N1—O1—C1—C2	169.7 (2)	C8—C9—C10—C5	−1.7 (4)
O1—N1—C4—C6	177.8 (2)	C14—C9—C10—C5	179.6 (3)
Cu1—N1—C4—C6	−10.2 (4)	O2—C5—C10—C11	−0.3 (4)
O1—N1—C4—C3	−0.1 (4)	C6—C5—C10—C11	179.0 (3)
Cu1—N1—C4—C3	171.9 (2)	O2—C5—C10—C9	178.8 (2)
Cu1—O2—C5—C6	26.8 (4)	C6—C5—C10—C9	−1.9 (4)
Cu1—O2—C5—C10	−153.96 (19)	C9—C10—C11—C12	0.0 (5)
O2—C5—C6—C7	−176.0 (3)	C5—C10—C11—C12	179.0 (3)
C10—C5—C6—C7	4.7 (4)	C10—C11—C12—C13	1.2 (5)
O2—C5—C6—C4	8.9 (4)	C11—C12—C13—C14	−0.8 (6)
C10—C5—C6—C4	−170.3 (2)	C12—C13—C14—C9	−0.7 (5)
N1—C4—C6—C5	−16.8 (4)	C8—C9—C14—C13	−176.9 (3)
C3—C4—C6—C5	161.2 (3)	C10—C9—C14—C13	1.7 (5)
N1—C4—C6—C7	168.2 (3)

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cg1ii	0.96	2.66	3.530 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Cg1i	0.96	2.66	3.530 (3)	151

Symmetry code: (i) .