Bis{N-[methoxy(4-methylbenzamido)methyl]-2,4-dimethylanilinido-κ²N,O}copper(II).

In the centrosymmetric mononuclear title complex, [Cu(C₁₈H₂₀N₂O₂)₂], the Cu(II) atom is four-coordinated in a trans-CuN₂O₂ square-planar geometry with the N-Cu-O chelate angle being 89.97 (11)°. The dihedral angles made by the planes defined by the aromatic ring carbons of the 4-methyl-benzene and 2,4-dimethyl-benzene fragments with the plane defined by the chelate ring are 13.43 (15) and 82.69 (13)° respectively. The angle between the planes defined by the aromatic carbons of the two rings is 89.40 (16)°. A a weak intra-molecular C-H⋯N hydrogen bond occurs.

Related literature

For applications of related compounds, see: Moro et al. (2009 ▶); Rauf et al. (2009 ▶); D’Cruz et al. (2003 ▶). For a related structure, see: Shen et al. (1999 ▶). For C—N bond lengths, see: Arslan et al. (2007 ▶).

Experimental

Crystal data

[Cu(C18H20N2O2)2]

M = 656.26

Triclinic,

a = 7.949 (2) Å

b = 10.191 (3) Å

c = 10.844 (4) Å

α = 80.784 (6)°

β = 74.302 (6)°

γ = 79.772 (6)°

V = 826.4 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.71 mm−1

T = 298 K

0.40 × 0.24 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.766, T max = 0.884

10650 measured reflections

3792 independent reflections

2609 reflections with I > 2/s(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.198

S = 1.01

3792 reflections

205 parameters

H-atom parameters constrained

Δρmax = 1.10 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I, 265R. DOI: 10.1107/S1600536812025081/qm2070sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025081/qm2070Isup2.hkl

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

[Cu(C18H20N2O2)2]	V = 826.4 (4) Å3
Mr = 656.26	Z = 1
Triclinic, P1	F(000) = 345
Hall symbol: -P 1	Dx = 1.319 Mg m−3
a = 7.949 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.191 (3) Å	θ = 2.0–27.5°
c = 10.844 (4) Å	µ = 0.71 mm−1
α = 80.784 (6)°	T = 298 K
β = 74.302 (6)°	Slab, dark green
γ = 79.772 (6)°	0.40 × 0.24 × 0.18 mm

Bruker SMART APEX CCD area-detector diffractometer	3792 independent reflections
Radiation source: fine-focus sealed tube	2609 reflections with I > 2/s(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 83.66 pixels mm-1	θmax = 27.5°, θmin = 2.0°
ω scan	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −13→13
Tmin = 0.766, Tmax = 0.884	l = −14→14
10650 measured reflections

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.1258P)2 + 0.1796P] where P = (Fo2 + 2Fc2)/3
3792 reflections	(Δ/σ)max < 0.001
205 parameters	Δρmax = 1.10 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.0000	0.5000	0.0000	0.0627 (3)
O1	−0.1657 (4)	0.3971 (2)	0.1152 (3)	0.0901 (10)
N2	−0.0057 (4)	0.1849 (3)	0.1172 (3)	0.0681 (8)
H2B	−0.0059	0.1033	0.1531	0.082*
N1	0.1674 (4)	0.3356 (3)	−0.0332 (3)	0.0656 (8)
C1	−0.3153 (5)	0.0812 (4)	0.2570 (4)	0.0821 (13)
H1A	−0.2125	0.0215	0.2332	0.098*
C2	−0.4700 (6)	0.0327 (4)	0.3219 (5)	0.1020 (17)
H2A	−0.4695	−0.0595	0.3429	0.122*
C3	−0.6273 (5)	0.1185 (4)	0.3570 (4)	0.0756 (11)
C4	−0.6217 (5)	0.2527 (4)	0.3283 (4)	0.0815 (12)
H4A	−0.7240	0.3124	0.3535	0.098*
C5	−0.4678 (5)	0.3015 (4)	0.2629 (4)	0.0791 (12)
H5A	−0.4689	0.3938	0.2423	0.095*
C6	−0.3110 (4)	0.2167 (3)	0.2269 (3)	0.0592 (8)
C7	−0.7988 (6)	0.0625 (6)	0.4239 (6)	0.1115 (19)
H7A	−0.8935	0.1353	0.4412	0.167*
H7B	−0.7873	0.0096	0.5035	0.167*
H7C	−0.8239	0.0073	0.3690	0.167*
C8	−0.1487 (4)	0.2717 (3)	0.1485 (3)	0.0589 (9)
C9	0.1395 (4)	0.2185 (3)	0.0320 (4)	0.0630 (9)
O3	0.2725 (3)	0.1187 (2)	0.0036 (3)	0.0813 (9)
C10	0.2530 (6)	−0.0141 (4)	0.0702 (5)	0.0887 (14)
H10A	0.3583	−0.0746	0.0400	0.133*
H10B	0.1542	−0.0441	0.0537	0.133*
H10C	0.2335	−0.0120	0.1612	0.133*
C11	0.3306 (4)	0.3394 (3)	−0.1320 (4)	0.0662 (10)
C12	0.4865 (5)	0.3460 (4)	−0.1022 (5)	0.0841 (13)
H12A	0.4905	0.3481	−0.0176	0.101*
C13	0.6398 (5)	0.3496 (4)	−0.2046 (6)	0.0915 (15)
H13A	0.7466	0.3515	−0.1856	0.110*
C14	0.6383 (6)	0.3502 (4)	−0.3302 (6)	0.0976 (17)
C15	0.4796 (6)	0.3439 (4)	−0.3572 (5)	0.0901 (14)
H15A	0.4755	0.3433	−0.4420	0.108*
C16	0.3248 (5)	0.3384 (4)	−0.2577 (5)	0.0763 (12)
C17	0.8026 (7)	0.3562 (6)	−0.4423 (6)	0.129 (2)
H17A	0.9024	0.3606	−0.4100	0.193*
H17B	0.7844	0.4346	−0.5021	0.193*
H17C	0.8241	0.2774	−0.4854	0.193*
C18	0.1646 (7)	0.3292 (7)	−0.2882 (6)	0.1151 (18)
H18A	0.0711	0.3267	−0.2106	0.173*
H18B	0.1778	0.2489	−0.3276	0.173*
H18C	0.1366	0.4060	−0.3469	0.173*

	U11	U22	U33	U12	U13	U23
Cu1	0.0487 (4)	0.0292 (3)	0.0850 (5)	−0.0033 (2)	0.0177 (3)	0.0044 (2)
O1	0.0619 (15)	0.0325 (11)	0.133 (2)	−0.0030 (10)	0.0375 (15)	0.0051 (13)
N2	0.0540 (16)	0.0318 (13)	0.093 (2)	−0.0040 (11)	0.0103 (14)	0.0142 (13)
N1	0.0492 (15)	0.0347 (13)	0.087 (2)	−0.0020 (11)	0.0173 (13)	0.0042 (12)
C1	0.067 (2)	0.0387 (17)	0.110 (3)	−0.0080 (16)	0.022 (2)	0.0062 (18)
C2	0.083 (3)	0.045 (2)	0.142 (4)	−0.021 (2)	0.034 (3)	−0.001 (2)
C3	0.067 (2)	0.064 (2)	0.079 (3)	−0.0243 (18)	0.0207 (18)	−0.0087 (19)
C4	0.061 (2)	0.060 (2)	0.096 (3)	−0.0054 (17)	0.0249 (19)	−0.008 (2)
C5	0.067 (2)	0.0414 (18)	0.102 (3)	−0.0108 (16)	0.022 (2)	−0.0004 (18)
C6	0.0580 (19)	0.0388 (16)	0.064 (2)	−0.0093 (13)	0.0105 (15)	0.0010 (14)
C7	0.076 (3)	0.104 (4)	0.132 (4)	−0.044 (3)	0.034 (3)	−0.018 (3)
C8	0.0538 (18)	0.0326 (14)	0.072 (2)	−0.0066 (13)	0.0112 (15)	0.0001 (13)
C9	0.0490 (17)	0.0349 (15)	0.086 (2)	−0.0020 (13)	0.0062 (16)	0.0032 (15)
O3	0.0555 (14)	0.0312 (11)	0.123 (2)	0.0030 (10)	0.0185 (14)	0.0111 (12)
C10	0.075 (3)	0.0341 (17)	0.125 (4)	0.0045 (16)	0.007 (2)	0.0141 (19)
C11	0.0522 (19)	0.0314 (14)	0.087 (3)	−0.0001 (13)	0.0195 (16)	0.0035 (15)
C12	0.048 (2)	0.048 (2)	0.128 (4)	−0.0017 (15)	0.008 (2)	0.014 (2)
C13	0.049 (2)	0.057 (2)	0.136 (4)	−0.0009 (17)	0.012 (2)	0.014 (2)
C14	0.066 (3)	0.048 (2)	0.134 (4)	0.0010 (18)	0.036 (3)	0.005 (2)
C15	0.086 (3)	0.058 (2)	0.098 (3)	−0.014 (2)	0.024 (2)	−0.004 (2)
C16	0.057 (2)	0.049 (2)	0.106 (3)	−0.0094 (16)	0.011 (2)	−0.0074 (19)
C17	0.074 (3)	0.103 (4)	0.154 (5)	−0.006 (3)	0.053 (3)	0.001 (3)
C18	0.100 (4)	0.120 (5)	0.123 (4)	−0.028 (4)	−0.015 (3)	−0.014 (4)

Cu1—O1	1.891 (2)	C7—H7C	0.9600
Cu1—O1i	1.891 (2)	C9—O3	1.338 (4)
Cu1—N1i	1.962 (3)	O3—C10	1.442 (4)
Cu1—N1	1.962 (3)	C10—H10A	0.9600
O1—C8	1.264 (4)	C10—H10B	0.9600
N2—C8	1.312 (4)	C10—H10C	0.9600
N2—C9	1.328 (4)	C11—C12	1.377 (6)
N2—H2B	0.8600	C11—C16	1.378 (6)
N1—C9	1.309 (4)	C12—C13	1.411 (6)
N1—C11	1.444 (4)	C12—H12A	0.9300
C1—C6	1.371 (5)	C13—C14	1.364 (8)
C1—C2	1.374 (5)	C13—H13A	0.9300
C1—H1A	0.9300	C14—C15	1.385 (7)
C2—C3	1.391 (6)	C14—C17	1.527 (6)
C2—H2A	0.9300	C15—C16	1.403 (5)
C3—C4	1.359 (6)	C15—H15A	0.9300
C3—C7	1.523 (5)	C16—C18	1.421 (7)
C4—C5	1.371 (5)	C17—H17A	0.9600
C4—H4A	0.9300	C17—H17B	0.9600
C5—C6	1.384 (5)	C17—H17C	0.9600
C5—H5A	0.9300	C18—H18A	0.9600
C6—C8	1.487 (4)	C18—H18B	0.9600
C7—H7A	0.9600	C18—H18C	0.9600
C7—H7B	0.9600
O1—Cu1—O1i	180.00 (13)	N1—C9—N2	128.6 (3)
O1—Cu1—N1i	90.03 (11)	N1—C9—O3	115.1 (3)
O1i—Cu1—N1i	89.97 (11)	N2—C9—O3	116.3 (3)
O1—Cu1—N1	89.97 (11)	C9—O3—C10	118.9 (3)
O1i—Cu1—N1	90.03 (11)	O3—C10—H10A	109.5
N1i—Cu1—N1	180.0	O3—C10—H10B	109.5
C8—O1—Cu1	128.5 (2)	H10A—C10—H10B	109.5
C8—N2—C9	122.4 (3)	O3—C10—H10C	109.5
C8—N2—H2B	118.8	H10A—C10—H10C	109.5
C9—N2—H2B	118.8	H10B—C10—H10C	109.5
C9—N1—C11	116.6 (3)	C12—C11—C16	121.0 (3)
C9—N1—Cu1	122.7 (2)	C12—C11—N1	121.2 (4)
C11—N1—Cu1	120.7 (2)	C16—C11—N1	117.7 (3)
C6—C1—C2	120.7 (4)	C11—C12—C13	117.6 (5)
C6—C1—H1A	119.6	C11—C12—H12A	121.2
C2—C1—H1A	119.6	C13—C12—H12A	121.2
C1—C2—C3	121.4 (4)	C14—C13—C12	122.9 (5)
C1—C2—H2A	119.3	C14—C13—H13A	118.5
C3—C2—H2A	119.3	C12—C13—H13A	118.5
C4—C3—C2	117.6 (3)	C13—C14—C15	118.2 (4)
C4—C3—C7	121.9 (4)	C13—C14—C17	123.5 (5)
C2—C3—C7	120.6 (4)	C15—C14—C17	118.3 (6)
C3—C4—C5	121.2 (4)	C14—C15—C16	120.5 (5)
C3—C4—H4A	119.4	C14—C15—H15A	119.7
C5—C4—H4A	119.4	C16—C15—H15A	119.7
C4—C5—C6	121.5 (4)	C11—C16—C15	119.8 (4)
C4—C5—H5A	119.2	C11—C16—C18	121.0 (4)
C6—C5—H5A	119.2	C15—C16—C18	119.2 (5)
C1—C6—C5	117.5 (3)	C14—C17—H17A	109.5
C1—C6—C8	121.9 (3)	C14—C17—H17B	109.5
C5—C6—C8	120.4 (3)	H17A—C17—H17B	109.5
C3—C7—H7A	109.5	C14—C17—H17C	109.5
C3—C7—H7B	109.5	H17A—C17—H17C	109.5
H7A—C7—H7B	109.5	H17B—C17—H17C	109.5
C3—C7—H7C	109.5	C16—C18—H18A	109.5
H7A—C7—H7C	109.5	C16—C18—H18B	109.5
H7B—C7—H7C	109.5	H18A—C18—H18B	109.5
O1—C8—N2	127.0 (3)	C16—C18—H18C	109.5
O1—C8—C6	116.1 (3)	H18A—C18—H18C	109.5
N2—C8—C6	116.8 (3)	H18B—C18—H18C	109.5
O1i—Cu1—O1—C8	104 (100)	C5—C6—C8—N2	−179.4 (4)
N1i—Cu1—O1—C8	−178.2 (4)	C11—N1—C9—N2	−172.2 (4)
N1—Cu1—O1—C8	1.8 (4)	Cu1—N1—C9—N2	8.3 (6)
O1—Cu1—N1—C9	−7.7 (4)	C11—N1—C9—O3	4.2 (6)
O1i—Cu1—N1—C9	172.3 (4)	Cu1—N1—C9—O3	−175.3 (3)
N1i—Cu1—N1—C9	−128 (100)	C8—N2—C9—N1	−0.1 (7)
O1—Cu1—N1—C11	172.8 (3)	C8—N2—C9—O3	−176.4 (4)
O1i—Cu1—N1—C11	−7.2 (3)	N1—C9—O3—C10	−179.6 (4)
N1i—Cu1—N1—C11	53 (100)	N2—C9—O3—C10	−2.8 (6)
C6—C1—C2—C3	1.3 (8)	C9—N1—C11—C12	−82.1 (5)
C1—C2—C3—C4	−2.0 (8)	Cu1—N1—C11—C12	97.4 (4)
C1—C2—C3—C7	177.4 (5)	C9—N1—C11—C16	99.0 (4)
C2—C3—C4—C5	2.4 (8)	Cu1—N1—C11—C16	−81.5 (4)
C7—C3—C4—C5	−177.0 (5)	C16—C11—C12—C13	−1.0 (5)
C3—C4—C5—C6	−2.0 (8)	N1—C11—C12—C13	−179.9 (3)
C2—C1—C6—C5	−0.8 (7)	C11—C12—C13—C14	1.8 (6)
C2—C1—C6—C8	−175.5 (4)	C12—C13—C14—C15	−1.6 (6)
C4—C5—C6—C1	1.1 (7)	C12—C13—C14—C17	179.0 (4)
C4—C5—C6—C8	175.9 (4)	C13—C14—C15—C16	0.6 (6)
Cu1—O1—C8—N2	5.3 (7)	C17—C14—C15—C16	−179.9 (4)
Cu1—O1—C8—C6	−171.8 (3)	C12—C11—C16—C15	0.2 (5)
C9—N2—C8—O1	−7.5 (7)	N1—C11—C16—C15	179.1 (3)
C9—N2—C8—C6	169.6 (4)	C12—C11—C16—C18	178.9 (4)
C1—C6—C8—O1	172.6 (4)	N1—C11—C16—C18	−2.2 (6)
C5—C6—C8—O1	−2.0 (6)	C14—C15—C16—C11	0.1 (6)
C1—C6—C8—N2	−4.9 (6)	C14—C15—C16—C18	−178.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···N1	0.96	2.27	2.783 (7)	112

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯N1	0.96	2.27	2.783 (7)	112