{4,4'-Dimeth-oxy-2,2'-[ethyl-enedioxy-bis(nitrilo-methyl-idyne)]diphenolato}copper(II).

The title complex, [Cu(C(18)H(18)N(2)O(6))], was synthesized by the reaction of copper(II) acetate mono-hydrate with the ligand 4,4'-dimeth-oxy-2,2'-[ethyl-enedioxy-bis(nitrilo-methyl-idyne)]diphenol (H(2)L). The Cu atom is coordinated by two O atoms and two N atoms of the L(2-) unit. A bridged dimer is formed through inter-molecular Cu⋯O inter-actions [Cu⋯O = 1.9408 (15) Å], creating a distorted square-pyramidal geometry about the Cu atoms.

Related literature

For related literature, see: Akine et al. (2001 ▶, 2005 ▶); Bhadbhade & Srinivas (1993 ▶); Garnovskii et al. (1993 ▶); Katsuki (1995 ▶); Ray et al. (2003 ▶); Sun et al. (2004 ▶); Sangeetha et al. (1999 ▶).

Experimental

Crystal data

[Cu(C18H18N2O6)]

M = 421.88

Monoclinic,

a = 15.453 (2) Å

b = 7.6408 (11) Å

c = 15.927 (2) Å

β = 107.686 (2)°

V = 1791.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.26 mm−1

T = 298 (2) K

0.51 × 0.29 × 0.20 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1996 ▶) T min = 0.566, T max = 0.787

8649 measured reflections

3138 independent reflections

2600 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.082

S = 1.10

3138 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.40 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807061752/pr2018sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061752/pr2018Isup2.hkl

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

[Cu(C18H18N2O6)]	F(000) = 868
Mr = 421.88	Dx = 1.564 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.453 (2) Å	Cell parameters from 4146 reflections
b = 7.6408 (11) Å	θ = 2.6–28.2°
c = 15.927 (2) Å	µ = 1.26 mm−1
β = 107.686 (2)°	T = 298 K
V = 1791.6 (4) Å3	Prismatic, brown
Z = 4	0.51 × 0.29 × 0.20 mm

Bruker APEX CCD area-detector diffractometer	3138 independent reflections
Radiation source: fine-focus sealed tube	2600 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000?)	h = −18→17
Tmin = 0.566, Tmax = 0.787	k = −9→9
8649 measured reflections	l = −11→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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0417P)2 + 0.4958P] where P = (Fo2 + 2Fc2)/3
3138 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.40 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	0.477290 (19)	−0.02861 (4)	0.592030 (18)	0.03177 (12)
N1	0.58032 (14)	−0.2027 (3)	0.63744 (13)	0.0346 (5)
N2	0.39767 (13)	−0.1437 (3)	0.65094 (12)	0.0322 (5)
O1	0.57217 (12)	−0.3861 (2)	0.64483 (13)	0.0489 (5)
O2	0.43329 (12)	−0.2799 (2)	0.71371 (10)	0.0390 (4)
O3	0.56375 (10)	0.1234 (2)	0.56144 (10)	0.0328 (4)
O4	0.91554 (12)	0.2546 (3)	0.76874 (13)	0.0552 (5)
O5	0.39007 (11)	0.1542 (2)	0.55425 (11)	0.0393 (4)
O6	0.03883 (14)	0.2491 (3)	0.56161 (17)	0.0680 (6)
C1	0.48180 (17)	−0.4460 (3)	0.60408 (17)	0.0406 (6)
H1A	0.4833	−0.5640	0.5821	0.049*
H1B	0.4523	−0.3711	0.5544	0.049*
C2	0.42871 (18)	−0.4441 (3)	0.66883 (17)	0.0400 (6)
H2A	0.3656	−0.4704	0.6379	0.048*
H2B	0.4516	−0.5356	0.7121	0.048*
C3	0.66344 (17)	−0.1582 (3)	0.67144 (17)	0.0380 (6)
H3	0.7040	−0.2446	0.7003	0.046*
C4	0.69934 (17)	0.0146 (3)	0.66865 (16)	0.0344 (6)
C5	0.64843 (15)	0.1439 (3)	0.61155 (15)	0.0307 (5)
C6	0.69354 (16)	0.3032 (3)	0.60920 (16)	0.0359 (6)
H6	0.6629	0.3910	0.5713	0.043*
C7	0.78087 (17)	0.3335 (4)	0.66068 (17)	0.0402 (6)
H7	0.8081	0.4405	0.6569	0.048*
C8	0.82935 (16)	0.2064 (4)	0.71851 (17)	0.0385 (6)
C9	0.78927 (17)	0.0474 (3)	0.72178 (17)	0.0390 (6)
H9	0.8216	−0.0394	0.7593	0.047*
C10	0.9674 (2)	0.1302 (5)	0.8288 (2)	0.0790 (11)
H10A	0.9378	0.1040	0.8723	0.118*
H10B	1.0267	0.1769	0.8573	0.118*
H10C	0.9728	0.0252	0.7977	0.118*
C11	0.31864 (17)	−0.0951 (3)	0.65357 (16)	0.0365 (6)
H11	0.2925	−0.1587	0.6894	0.044*
C12	0.26844 (17)	0.0485 (3)	0.60588 (16)	0.0356 (6)
C13	0.30721 (16)	0.1661 (3)	0.55881 (15)	0.0343 (6)
C14	0.25243 (17)	0.3072 (3)	0.51642 (18)	0.0428 (6)
H14	0.2758	0.3865	0.4847	0.051*
C15	0.16610 (18)	0.3314 (4)	0.52042 (18)	0.0455 (7)
H15	0.1325	0.4275	0.4926	0.055*
C16	0.12811 (18)	0.2130 (4)	0.56585 (19)	0.0468 (7)
C17	0.17833 (18)	0.0747 (4)	0.60834 (19)	0.0448 (7)
H17	0.1533	−0.0034	0.6393	0.054*
C18	−0.0041 (2)	0.1304 (6)	0.6035 (3)	0.0805 (11)
H18A	−0.0043	0.0160	0.5785	0.121*
H18B	−0.0654	0.1676	0.5953	0.121*
H18C	0.0282	0.1265	0.6653	0.121*

	U11	U22	U33	U12	U13	U23
Cu1	0.03453 (18)	0.02879 (19)	0.03462 (18)	−0.00140 (12)	0.01445 (13)	0.00478 (13)
N1	0.0442 (12)	0.0240 (11)	0.0385 (11)	0.0009 (9)	0.0168 (10)	0.0044 (9)
N2	0.0400 (12)	0.0291 (11)	0.0285 (10)	−0.0012 (9)	0.0121 (9)	0.0061 (8)
O1	0.0487 (11)	0.0240 (10)	0.0756 (14)	0.0007 (8)	0.0214 (10)	0.0039 (9)
O2	0.0503 (11)	0.0383 (10)	0.0293 (9)	0.0032 (8)	0.0134 (8)	0.0098 (8)
O3	0.0297 (9)	0.0335 (10)	0.0346 (9)	−0.0040 (7)	0.0087 (7)	0.0067 (7)
O4	0.0374 (10)	0.0574 (13)	0.0605 (13)	−0.0028 (9)	−0.0005 (9)	−0.0010 (10)
O5	0.0391 (10)	0.0341 (10)	0.0492 (10)	0.0004 (8)	0.0200 (8)	0.0108 (8)
O6	0.0435 (12)	0.0683 (15)	0.0981 (17)	0.0101 (10)	0.0303 (12)	0.0139 (13)
C1	0.0563 (17)	0.0255 (14)	0.0393 (15)	−0.0066 (12)	0.0133 (13)	−0.0008 (11)
C2	0.0448 (15)	0.0320 (15)	0.0406 (14)	−0.0043 (11)	0.0091 (12)	0.0109 (11)
C3	0.0418 (15)	0.0312 (14)	0.0419 (14)	0.0063 (11)	0.0139 (12)	0.0064 (11)
C4	0.0382 (14)	0.0315 (14)	0.0361 (13)	0.0025 (10)	0.0150 (11)	0.0008 (11)
C5	0.0327 (13)	0.0320 (14)	0.0307 (12)	0.0004 (10)	0.0145 (10)	−0.0011 (10)
C6	0.0341 (13)	0.0335 (14)	0.0398 (14)	−0.0005 (11)	0.0107 (11)	0.0082 (11)
C7	0.0375 (14)	0.0357 (15)	0.0492 (16)	−0.0058 (11)	0.0159 (12)	−0.0001 (12)
C8	0.0297 (13)	0.0452 (16)	0.0397 (14)	−0.0004 (11)	0.0094 (11)	−0.0056 (12)
C9	0.0379 (14)	0.0384 (16)	0.0388 (14)	0.0083 (11)	0.0089 (11)	0.0040 (11)
C10	0.0525 (19)	0.085 (3)	0.078 (2)	−0.0001 (18)	−0.0126 (18)	0.013 (2)
C11	0.0413 (15)	0.0361 (15)	0.0359 (14)	−0.0056 (11)	0.0175 (12)	0.0042 (11)
C12	0.0367 (13)	0.0349 (15)	0.0359 (13)	−0.0037 (11)	0.0122 (11)	−0.0007 (11)
C13	0.0364 (13)	0.0329 (14)	0.0323 (13)	−0.0056 (11)	0.0086 (11)	−0.0012 (11)
C14	0.0418 (15)	0.0362 (15)	0.0478 (16)	−0.0037 (12)	0.0097 (12)	0.0091 (12)
C15	0.0411 (15)	0.0378 (16)	0.0508 (16)	0.0015 (12)	0.0040 (13)	0.0031 (13)
C16	0.0350 (14)	0.0495 (18)	0.0562 (17)	−0.0001 (12)	0.0145 (13)	−0.0043 (14)
C17	0.0425 (15)	0.0445 (17)	0.0513 (16)	−0.0038 (12)	0.0204 (13)	0.0047 (13)
C18	0.058 (2)	0.090 (3)	0.110 (3)	0.0051 (19)	0.052 (2)	0.010 (2)

Cu1—O5	1.9068 (17)	C5—C6	1.409 (3)
Cu1—O3	1.9408 (15)	C6—C7	1.369 (3)
Cu1—N2	1.9670 (19)	C6—H6	0.9300
Cu1—N1	2.032 (2)	C7—C8	1.390 (4)
N1—C3	1.279 (3)	C7—H7	0.9300
N1—O1	1.415 (3)	C8—C9	1.372 (4)
N2—C11	1.289 (3)	C9—H9	0.9300
N2—O2	1.432 (2)	C10—H10A	0.9600
O1—C1	1.425 (3)	C10—H10B	0.9600
O2—C2	1.435 (3)	C10—H10C	0.9600
O3—C5	1.319 (3)	C11—C12	1.423 (4)
O4—C8	1.379 (3)	C11—H11	0.9300
O4—C10	1.412 (4)	C12—C13	1.415 (3)
O5—C13	1.308 (3)	C12—C17	1.419 (4)
O6—C16	1.388 (3)	C13—C14	1.410 (3)
O6—C18	1.406 (4)	C14—C15	1.367 (4)
C1—C2	1.500 (3)	C14—H14	0.9300
C1—H1A	0.9700	C15—C16	1.395 (4)
C1—H1B	0.9700	C15—H15	0.9300
C2—H2A	0.9700	C16—C17	1.363 (4)
C2—H2B	0.9700	C17—H17	0.9300
C3—C4	1.438 (3)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C4—C5	1.410 (3)	C18—H18C	0.9600
C4—C9	1.413 (4)
O5—Cu1—O3	87.53 (7)	C6—C7—C8	120.9 (2)
O5—Cu1—N2	89.62 (8)	C6—C7—H7	119.5
O3—Cu1—N2	164.87 (8)	C8—C7—H7	119.5
O5—Cu1—N1	173.80 (8)	C9—C8—O4	125.6 (2)
O3—Cu1—N1	87.50 (7)	C9—C8—C7	119.0 (2)
N2—Cu1—N1	94.22 (8)	O4—C8—C7	115.4 (2)
C3—N1—O1	109.3 (2)	C8—C9—C4	120.5 (2)
C3—N1—Cu1	123.67 (17)	C8—C9—H9	119.7
O1—N1—Cu1	126.72 (15)	C4—C9—H9	119.7
C11—N2—O2	110.71 (18)	O4—C10—H10A	109.5
C11—N2—Cu1	128.51 (17)	O4—C10—H10B	109.5
O2—N2—Cu1	119.63 (14)	H10A—C10—H10B	109.5
N1—O1—C1	112.32 (18)	O4—C10—H10C	109.5
N2—O2—C2	109.72 (16)	H10A—C10—H10C	109.5
C5—O3—Cu1	123.45 (14)	H10B—C10—H10C	109.5
C8—O4—C10	117.5 (2)	N2—C11—C12	125.0 (2)
C13—O5—Cu1	130.08 (15)	N2—C11—H11	117.5
C16—O6—C18	117.0 (2)	C12—C11—H11	117.5
O1—C1—C2	110.4 (2)	C13—C12—C17	120.1 (2)
O1—C1—H1A	109.6	C13—C12—C11	121.5 (2)
C2—C1—H1A	109.6	C17—C12—C11	118.3 (2)
O1—C1—H1B	109.6	O5—C13—C14	118.8 (2)
C2—C1—H1B	109.6	O5—C13—C12	124.4 (2)
H1A—C1—H1B	108.1	C14—C13—C12	116.8 (2)
O2—C2—C1	113.3 (2)	C15—C14—C13	122.3 (2)
O2—C2—H2A	108.9	C15—C14—H14	118.9
C1—C2—H2A	108.9	C13—C14—H14	118.9
O2—C2—H2B	108.9	C14—C15—C16	120.5 (3)
C1—C2—H2B	108.9	C14—C15—H15	119.8
H2A—C2—H2B	107.7	C16—C15—H15	119.8
N1—C3—C4	125.3 (2)	C17—C16—O6	125.8 (3)
N1—C3—H3	117.3	C17—C16—C15	119.6 (2)
C4—C3—H3	117.3	O6—C16—C15	114.5 (3)
C5—C4—C9	121.1 (2)	C16—C17—C12	120.7 (2)
C5—C4—C3	121.2 (2)	C16—C17—H17	119.6
C9—C4—C3	117.6 (2)	C12—C17—H17	119.6
O3—C5—C6	119.6 (2)	O6—C18—H18A	109.5
O3—C5—C4	124.3 (2)	O6—C18—H18B	109.5
C6—C5—C4	116.0 (2)	H18A—C18—H18B	109.5
C7—C6—C5	122.4 (2)	O6—C18—H18C	109.5
C7—C6—H6	118.8	H18A—C18—H18C	109.5
C5—C6—H6	118.8	H18B—C18—H18C	109.5
O5—Cu1—N1—C3	−5.1 (8)	C3—C4—C5—C6	−174.8 (2)
O3—Cu1—N1—C3	31.6 (2)	O3—C5—C6—C7	178.9 (2)
N2—Cu1—N1—C3	−133.3 (2)	C4—C5—C6—C7	−1.6 (4)
O5—Cu1—N1—O1	168.3 (6)	C5—C6—C7—C8	−0.2 (4)
O3—Cu1—N1—O1	−154.89 (18)	C10—O4—C8—C9	0.0 (4)
N2—Cu1—N1—O1	40.17 (19)	C10—O4—C8—C7	179.7 (3)
O5—Cu1—N2—C11	1.3 (2)	C6—C7—C8—C9	1.7 (4)
O3—Cu1—N2—C11	80.4 (4)	C6—C7—C8—O4	−178.0 (2)
N1—Cu1—N2—C11	176.4 (2)	O4—C8—C9—C4	178.3 (2)
O5—Cu1—N2—O2	−165.28 (15)	C7—C8—C9—C4	−1.4 (4)
O3—Cu1—N2—O2	−86.2 (3)	C5—C4—C9—C8	−0.4 (4)
N1—Cu1—N2—O2	9.85 (16)	C3—C4—C9—C8	176.4 (2)
C3—N1—O1—C1	−177.0 (2)	O2—N2—C11—C12	173.7 (2)
Cu1—N1—O1—C1	8.8 (3)	Cu1—N2—C11—C12	6.2 (4)
C11—N2—O2—C2	106.1 (2)	N2—C11—C12—C13	−8.2 (4)
Cu1—N2—O2—C2	−85.07 (19)	N2—C11—C12—C17	173.5 (2)
O5—Cu1—O3—C5	136.42 (18)	Cu1—O5—C13—C14	−172.55 (17)
N2—Cu1—O3—C5	57.1 (4)	Cu1—O5—C13—C12	9.2 (4)
N1—Cu1—O3—C5	−39.87 (18)	C17—C12—C13—O5	178.7 (2)
O3—Cu1—O5—C13	−174.0 (2)	C11—C12—C13—O5	0.4 (4)
N2—Cu1—O5—C13	−8.9 (2)	C17—C12—C13—C14	0.4 (4)
N1—Cu1—O5—C13	−137.2 (6)	C11—C12—C13—C14	−177.9 (2)
N1—O1—C1—C2	−89.8 (2)	O5—C13—C14—C15	−178.0 (2)
N2—O2—C2—C1	60.0 (3)	C12—C13—C14—C15	0.3 (4)
O1—C1—C2—O2	51.2 (3)	C13—C14—C15—C16	−1.4 (4)
O1—N1—C3—C4	173.7 (2)	C18—O6—C16—C17	−1.3 (5)
Cu1—N1—C3—C4	−11.9 (4)	C18—O6—C16—C15	177.7 (3)
N1—C3—C4—C5	−13.5 (4)	C14—C15—C16—C17	1.6 (4)
N1—C3—C4—C9	169.8 (2)	C14—C15—C16—O6	−177.4 (3)
Cu1—O3—C5—C6	−151.11 (17)	O6—C16—C17—C12	178.1 (3)
Cu1—O3—C5—C4	29.4 (3)	C15—C16—C17—C12	−0.8 (4)
C9—C4—C5—O3	−178.7 (2)	C13—C12—C17—C16	−0.2 (4)
C3—C4—C5—O3	4.7 (4)	C11—C12—C17—C16	178.2 (3)
C9—C4—C5—C6	1.8 (3)