Bis{μ-2,4-di-tert-butyl-6-[3-(1H-imidazol-1-yl)propyl-imino-meth-yl]phenolato}bis-[acetatocopper(II)].

In the centrosymmetric title compound, [Cu(2)(C(21)H(30)N(3)O)(2)(C(2)H(3)O(2))(2)], each Cu atom has a distorted tetra-hedral coordination geometry defined by N and O atoms in a chelate ring, N of an imidazole ring, and an acetate O atom. The uncoordinated acetate O atom is disordered over two sites with occupancies 0.7:0.3.

Related literature

For related literature, see: Djebbar et al. (1997 ▶); Hansen et al. (1996 ▶); Huang et al. (2002 ▶); Lacroix et al. (2004 ▶); Tas et al. (2004 ▶).

Experimental

Crystal data

[Cu2(C21H30N3O)2(C2H3O2)2]

M = 926.13

Monoclinic,

a = 14.1745 (11) Å

b = 10.2898 (8) Å

c = 19.0850 (17) Å

β = 116.502 (6)°

V = 2491.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.90 mm−1

T = 296 K

0.25 × 0.19 × 0.07 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.741, T max = 0.914

34842 measured reflections

4905 independent reflections

2485 reflections with I > 2σ(I)

R int = 0.167

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.128

S = 0.95

4905 reflections

275 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.24 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063283/cf2164sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063283/cf2164Isup2.hkl

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

[Cu2(C21H30N3O)2(C2H3O2)2]	F000 = 980
Mr = 926.13	Dx = 1.235 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 29181 reflections
a = 14.1745 (11) Å	θ = 1.6–27.9º
b = 10.2898 (8) Å	µ = 0.90 mm−1
c = 19.0850 (17) Å	T = 296 K
β = 116.502 (6)º	Prism, black
V = 2491.1 (4) Å3	0.25 × 0.19 × 0.07 mm
Z = 2

STOE IPDSII diffractometer	4905 independent reflections
Radiation source: fine-focus sealed tube	2485 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.167
Detector resolution: 6.67 pixels mm-1	θmax = 26.0º
T = 296 K	θmin = 2.2º
rotation method scans	h = −17→17
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)	k = −12→12
Tmin = 0.741, Tmax = 0.914	l = −23→23
34842 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0447P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max < 0.001
4905 reflections	Δρmax = 0.31 e Å−3
275 parameters	Δρmin = −0.24 e Å−3
12 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
C1	0.6847 (4)	0.6496 (5)	0.4074 (3)	0.0479 (12)
C2	0.6890 (4)	0.5548 (4)	0.3558 (3)	0.0478 (12)
C3	0.7777 (4)	0.5428 (5)	0.3420 (3)	0.0573 (14)
H3	0.7789	0.4768	0.3092	0.069*
C4	0.8623 (4)	0.6239 (5)	0.3749 (3)	0.0570 (14)
C5	0.8573 (4)	0.7181 (6)	0.4260 (3)	0.0635 (15)
H5	0.9142	0.7745	0.4491	0.076*
C6	0.7738 (4)	0.7346 (5)	0.4451 (3)	0.0531 (13)
C7	0.6028 (4)	0.4685 (5)	0.3117 (3)	0.0556 (13)
H7	0.6150	0.4070	0.2810	0.067*
C8	0.9600 (5)	0.6182 (6)	0.3599 (4)	0.0752 (17)
C9	0.9519 (6)	0.5078 (8)	0.3043 (6)	0.141 (4)
H9A	0.9468	0.4264	0.3269	0.169*
H9B	1.0136	0.5074	0.2955	0.169*
H9C	0.8904	0.5200	0.2554	0.169*
C10	0.9705 (7)	0.7427 (8)	0.3223 (5)	0.131 (3)
H10A	1.0295	0.7362	0.3105	0.157*
H10B	0.9814	0.8139	0.3576	0.157*
H10C	0.9073	0.7573	0.2748	0.157*
C11	1.0571 (5)	0.5926 (11)	0.4350 (5)	0.156 (4)
H11A	1.0500	0.5106	0.4563	0.187*
H11B	1.0656	0.6605	0.4719	0.187*
H11C	1.1177	0.5902	0.4250	0.187*
C12	0.7780 (4)	0.8338 (6)	0.5050 (3)	0.0671 (15)
C13	0.8787 (5)	0.9195 (8)	0.5362 (4)	0.113 (3)
H13A	0.8786	0.9778	0.5754	0.136*
H13B	0.8796	0.9687	0.4938	0.136*
H13C	0.9400	0.8650	0.5586	0.136*
C14	0.6846 (5)	0.9279 (6)	0.4704 (3)	0.0811 (17)
H14A	0.6199	0.8802	0.4537	0.097*
H14B	0.6853	0.9722	0.4264	0.097*
H14C	0.6900	0.9903	0.5094	0.097*
C15	0.7796 (5)	0.7619 (7)	0.5764 (3)	0.0817 (18)
H15A	0.7156	0.7132	0.5605	0.098*
H15B	0.7854	0.8240	0.6157	0.098*
H15C	0.8388	0.7039	0.5974	0.098*
C16	0.4370 (4)	0.3671 (5)	0.2586 (3)	0.0649 (16)
H16A	0.4696	0.3215	0.2306	0.078*
H16B	0.3740	0.4095	0.2203	0.078*
C17	0.4064 (5)	0.2697 (6)	0.3046 (3)	0.0698 (17)
H17A	0.3537	0.2114	0.2679	0.084*
H17B	0.3742	0.3162	0.3326	0.084*
C18	0.5027 (5)	0.8115 (6)	0.6368 (4)	0.0771 (18)
H18A	0.4521	0.8271	0.6571	0.092*
H18B	0.5294	0.8949	0.6300	0.092*
C19	0.4943 (4)	0.7166 (5)	0.5142 (3)	0.0657 (15)
H19	0.5638	0.7362	0.5260	0.079*
C20	0.3381 (4)	0.6471 (6)	0.4573 (3)	0.0665 (15)
H20	0.2764	0.6086	0.4207	0.080*
C21	0.3507 (5)	0.7013 (6)	0.5248 (4)	0.0705 (16)
H21	0.3002	0.7066	0.5433	0.085*
C22	0.2820 (5)	0.6256 (6)	0.2458 (4)	0.0721 (17)
C23	0.1666 (5)	0.6146 (8)	0.1897 (4)	0.122 (3)
H23A	0.1251	0.6322	0.2169	0.146*
H23B	0.1518	0.5283	0.1683	0.146*
H23C	0.1493	0.6763	0.1480	0.146*
N1	0.5106 (3)	0.4662 (4)	0.3098 (2)	0.0543 (11)
N2	0.4498 (4)	0.7462 (4)	0.5607 (3)	0.0620 (12)
N3	0.4297 (3)	0.6572 (4)	0.4504 (2)	0.0596 (11)
O1	0.6027 (2)	0.6631 (3)	0.42159 (19)	0.0557 (9)
O2	0.3149 (3)	0.5524 (4)	0.3042 (2)	0.0705 (11)
O3A	0.327 (3)	0.721 (4)	0.253 (2)	0.105 (5)	0.30 (4)
O3B	0.3390 (11)	0.6916 (16)	0.2238 (13)	0.105 (5)	0.70 (4)
Cu1	0.46586 (5)	0.58707 (6)	0.36829 (4)	0.0531 (2)

	U11	U22	U33	U12	U13	U23
C1	0.035 (3)	0.061 (3)	0.044 (3)	0.006 (2)	0.014 (2)	0.010 (2)
C2	0.041 (3)	0.054 (3)	0.051 (3)	0.006 (2)	0.022 (2)	0.006 (2)
C3	0.056 (3)	0.065 (4)	0.060 (3)	0.020 (3)	0.033 (3)	0.019 (3)
C4	0.040 (3)	0.064 (4)	0.069 (3)	0.011 (2)	0.026 (3)	0.020 (3)
C5	0.035 (3)	0.081 (4)	0.068 (4)	−0.001 (3)	0.018 (3)	0.014 (3)
C6	0.037 (3)	0.064 (3)	0.052 (3)	0.001 (2)	0.014 (2)	0.007 (3)
C7	0.058 (3)	0.066 (4)	0.046 (3)	0.005 (3)	0.026 (3)	0.001 (2)
C8	0.056 (3)	0.093 (5)	0.092 (4)	0.007 (3)	0.047 (3)	0.020 (4)
C9	0.119 (7)	0.128 (7)	0.242 (11)	0.001 (5)	0.141 (8)	−0.009 (8)
C10	0.145 (7)	0.129 (7)	0.175 (8)	−0.003 (6)	0.121 (7)	0.028 (6)
C11	0.059 (4)	0.294 (13)	0.134 (6)	0.047 (7)	0.061 (5)	0.069 (8)
C12	0.052 (3)	0.077 (4)	0.067 (4)	−0.010 (3)	0.022 (3)	−0.005 (3)
C13	0.090 (5)	0.139 (7)	0.117 (5)	−0.054 (5)	0.052 (4)	−0.053 (5)
C14	0.089 (4)	0.066 (4)	0.087 (4)	−0.005 (4)	0.037 (4)	−0.014 (3)
C15	0.065 (4)	0.113 (5)	0.052 (3)	0.014 (4)	0.014 (3)	−0.002 (3)
C16	0.063 (4)	0.077 (4)	0.055 (3)	−0.008 (3)	0.026 (3)	−0.023 (3)
C17	0.071 (4)	0.075 (4)	0.073 (4)	−0.029 (3)	0.040 (3)	−0.039 (3)
C18	0.100 (5)	0.061 (4)	0.089 (4)	0.000 (3)	0.059 (4)	−0.024 (3)
C19	0.053 (3)	0.085 (4)	0.070 (4)	−0.011 (3)	0.036 (3)	−0.020 (3)
C20	0.046 (3)	0.085 (4)	0.072 (4)	−0.007 (3)	0.029 (3)	−0.006 (3)
C21	0.063 (4)	0.086 (4)	0.081 (4)	−0.002 (3)	0.049 (3)	−0.012 (3)
C22	0.054 (4)	0.067 (5)	0.092 (5)	0.001 (3)	0.029 (4)	0.002 (4)
C23	0.063 (4)	0.150 (8)	0.110 (5)	−0.001 (5)	0.001 (4)	0.012 (5)
N1	0.046 (2)	0.069 (3)	0.047 (2)	−0.002 (2)	0.020 (2)	−0.003 (2)
N2	0.063 (3)	0.064 (3)	0.070 (3)	−0.002 (2)	0.039 (3)	−0.014 (2)
N3	0.044 (3)	0.078 (3)	0.062 (3)	−0.002 (2)	0.028 (2)	−0.012 (2)
O1	0.0381 (19)	0.073 (2)	0.058 (2)	−0.0021 (16)	0.0235 (17)	−0.0077 (17)
O2	0.048 (2)	0.096 (3)	0.068 (2)	−0.004 (2)	0.0253 (19)	−0.007 (2)
O3A	0.079 (5)	0.092 (7)	0.162 (12)	0.008 (4)	0.070 (6)	0.041 (7)
O3B	0.079 (5)	0.092 (7)	0.162 (12)	0.008 (4)	0.070 (6)	0.041 (7)
Cu1	0.0392 (3)	0.0685 (4)	0.0521 (3)	−0.0025 (4)	0.0207 (2)	−0.0072 (4)

C1—O1	1.313 (5)	C14—H14C	0.960
C1—C2	1.407 (6)	C15—H15A	0.960
C1—C6	1.439 (7)	C15—H15B	0.960
C2—C3	1.399 (6)	C15—H15C	0.960
C2—C7	1.440 (7)	C16—N1	1.474 (6)
C3—C4	1.363 (7)	C16—C17	1.517 (7)
C3—H3	0.930	C16—H16A	0.970
C4—C5	1.400 (7)	C16—H16B	0.970
C4—C8	1.535 (7)	C17—C18i	1.524 (8)
C5—C6	1.395 (7)	C17—H17A	0.970
C5—H5	0.930	C17—H17B	0.970
C6—C12	1.514 (7)	C18—N2	1.467 (7)
C7—N1	1.291 (6)	C18—C17i	1.524 (8)
C7—H7	0.930	C18—H18A	0.970
C8—C11	1.503 (9)	C18—H18B	0.970
C8—C10	1.508 (9)	C19—N3	1.304 (6)
C8—C9	1.524 (10)	C19—N2	1.331 (6)
C9—H9A	0.960	C19—H19	0.930
C9—H9B	0.960	C20—C21	1.341 (7)
C9—H9C	0.960	C20—N3	1.366 (6)
C10—H10A	0.960	C20—H20	0.930
C10—H10B	0.960	C21—N2	1.341 (7)
C10—H10C	0.960	C21—H21	0.930
C11—H11A	0.960	C22—O3A	1.14 (4)
C11—H11B	0.960	C22—O2	1.249 (7)
C11—H11C	0.960	C22—O3B	1.263 (18)
C12—C14	1.532 (8)	C22—C23	1.509 (8)
C12—C15	1.541 (8)	C23—H23A	0.960
C12—C13	1.552 (8)	C23—H23B	0.960
C13—H13A	0.960	C23—H23C	0.960
C13—H13B	0.960	N1—Cu1	1.957 (4)
C13—H13C	0.960	N3—Cu1	1.989 (4)
C14—H14A	0.960	O1—Cu1	1.910 (3)
C14—H14B	0.960	O2—Cu1	1.966 (3)
O1—C1—C2	122.5 (4)	H14B—C14—H14C	109.5
O1—C1—C6	119.5 (4)	C12—C15—H15A	109.5
C2—C1—C6	118.0 (4)	C12—C15—H15B	109.5
C3—C2—C1	121.1 (5)	H15A—C15—H15B	109.5
C3—C2—C7	115.8 (5)	C12—C15—H15C	109.5
C1—C2—C7	123.1 (4)	H15A—C15—H15C	109.5
C4—C3—C2	122.7 (5)	H15B—C15—H15C	109.5
C4—C3—H3	118.7	N1—C16—C17	112.0 (4)
C2—C3—H3	118.7	N1—C16—H16A	109.2
C3—C4—C5	115.9 (5)	C17—C16—H16A	109.2
C3—C4—C8	125.0 (5)	N1—C16—H16B	109.2
C5—C4—C8	119.2 (5)	C17—C16—H16B	109.2
C6—C5—C4	125.4 (5)	H16A—C16—H16B	107.9
C6—C5—H5	117.3	C16—C17—C18i	114.9 (5)
C4—C5—H5	117.3	C16—C17—H17A	108.5
C5—C6—C1	116.9 (5)	C18i—C17—H17A	108.5
C5—C6—C12	121.8 (5)	C16—C17—H17B	108.5
C1—C6—C12	121.2 (4)	C18i—C17—H17B	108.5
N1—C7—C2	127.8 (5)	H17A—C17—H17B	107.5
N1—C7—H7	116.1	N2—C18—C17i	111.5 (4)
C2—C7—H7	116.1	N2—C18—H18A	109.3
C11—C8—C10	111.1 (7)	C17i—C18—H18A	109.3
C11—C8—C9	106.6 (6)	N2—C18—H18B	109.3
C10—C8—C9	107.1 (6)	C17i—C18—H18B	109.3
C11—C8—C4	110.3 (5)	H18A—C18—H18B	108.0
C10—C8—C4	110.2 (5)	N3—C19—N2	112.7 (5)
C9—C8—C4	111.4 (5)	N3—C19—H19	123.7
C8—C9—H9A	109.5	N2—C19—H19	123.7
C8—C9—H9B	109.5	C21—C20—N3	109.7 (5)
H9A—C9—H9B	109.5	C21—C20—H20	125.2
C8—C9—H9C	109.5	N3—C20—H20	125.2
H9A—C9—H9C	109.5	C20—C21—N2	107.1 (5)
H9B—C9—H9C	109.5	C20—C21—H21	126.5
C8—C10—H10A	109.5	N2—C21—H21	126.5
C8—C10—H10B	109.5	O3A—C22—O2	116 (2)
H10A—C10—H10B	109.5	O2—C22—O3B	125.6 (8)
C8—C10—H10C	109.5	O3A—C22—C23	121.2 (19)
H10A—C10—H10C	109.5	O2—C22—C23	116.3 (6)
H10B—C10—H10C	109.5	O3B—C22—C23	117.1 (9)
C8—C11—H11A	109.5	C22—C23—H23A	109.5
C8—C11—H11B	109.5	C22—C23—H23B	109.5
H11A—C11—H11B	109.5	H23A—C23—H23B	109.5
C8—C11—H11C	109.5	C22—C23—H23C	109.5
H11A—C11—H11C	109.5	H23A—C23—H23C	109.5
H11B—C11—H11C	109.5	H23B—C23—H23C	109.5
C6—C12—C14	111.4 (4)	C7—N1—C16	116.1 (4)
C6—C12—C15	108.9 (5)	C7—N1—Cu1	123.6 (3)
C14—C12—C15	110.7 (5)	C16—N1—Cu1	120.2 (3)
C6—C12—C13	113.1 (5)	C19—N2—C21	106.3 (5)
C14—C12—C13	106.0 (5)	C19—N2—C18	125.4 (5)
C15—C12—C13	106.6 (5)	C21—N2—C18	128.3 (5)
C12—C13—H13A	109.5	C19—N3—C20	104.3 (4)
C12—C13—H13B	109.5	C19—N3—Cu1	125.8 (4)
H13A—C13—H13B	109.5	C20—N3—Cu1	129.7 (4)
C12—C13—H13C	109.5	C1—O1—Cu1	128.9 (3)
H13A—C13—H13C	109.5	C22—O2—Cu1	108.4 (4)
H13B—C13—H13C	109.5	O1—Cu1—N1	93.07 (15)
C12—C14—H14A	109.5	O1—Cu1—O2	165.98 (17)
C12—C14—H14B	109.5	N1—Cu1—O2	93.98 (16)
H14A—C14—H14B	109.5	O1—Cu1—N3	89.40 (16)
C12—C14—H14C	109.5	N1—Cu1—N3	160.63 (17)
H14A—C14—H14C	109.5	O2—Cu1—N3	87.95 (16)
O1—C1—C2—C3	−179.9 (4)	C17—C16—N1—Cu1	−64.3 (5)
C6—C1—C2—C3	0.5 (6)	N3—C19—N2—C21	0.8 (7)
O1—C1—C2—C7	2.7 (7)	N3—C19—N2—C18	179.1 (5)
C6—C1—C2—C7	−176.9 (4)	C20—C21—N2—C19	−0.7 (7)
C1—C2—C3—C4	−2.5 (7)	C20—C21—N2—C18	−178.9 (5)
C7—C2—C3—C4	175.1 (4)	C17i—C18—N2—C19	−62.9 (7)
C2—C3—C4—C5	2.3 (7)	C17i—C18—N2—C21	115.0 (6)
C2—C3—C4—C8	−177.9 (5)	N2—C19—N3—C20	−0.7 (6)
C3—C4—C5—C6	−0.1 (7)	N2—C19—N3—Cu1	−176.3 (4)
C8—C4—C5—C6	−179.9 (5)	C21—C20—N3—C19	0.2 (6)
C4—C5—C6—C1	−1.8 (7)	C21—C20—N3—Cu1	175.6 (4)
C4—C5—C6—C12	176.1 (5)	C2—C1—O1—Cu1	−11.4 (6)
O1—C1—C6—C5	−178.2 (4)	C6—C1—O1—Cu1	168.3 (3)
C2—C1—C6—C5	1.5 (6)	O3A—C22—O2—Cu1	−26 (2)
O1—C1—C6—C12	4.0 (7)	O3B—C22—O2—Cu1	12.5 (16)
C2—C1—C6—C12	−176.4 (4)	C23—C22—O2—Cu1	−179.2 (5)
C3—C2—C7—N1	−174.9 (5)	C1—O1—Cu1—N1	11.6 (4)
C1—C2—C7—N1	2.6 (8)	C1—O1—Cu1—O2	−108.6 (7)
C3—C4—C8—C11	−119.3 (7)	C1—O1—Cu1—N3	172.3 (4)
C5—C4—C8—C11	60.5 (7)	C7—N1—Cu1—O1	−6.0 (4)
C3—C4—C8—C10	117.7 (6)	C16—N1—Cu1—O1	175.3 (4)
C5—C4—C8—C10	−62.5 (7)	C7—N1—Cu1—O2	161.9 (4)
C3—C4—C8—C9	−1.1 (8)	C16—N1—Cu1—O2	−16.9 (4)
C5—C4—C8—C9	178.7 (6)	C7—N1—Cu1—N3	−103.0 (6)
C5—C6—C12—C14	123.9 (5)	C16—N1—Cu1—N3	78.3 (6)
C1—C6—C12—C14	−58.3 (7)	C22—O2—Cu1—O1	33.7 (8)
C5—C6—C12—C15	−113.7 (5)	C22—O2—Cu1—N1	−86.3 (4)
C1—C6—C12—C15	64.1 (6)	C22—O2—Cu1—N3	113.0 (4)
C5—C6—C12—C13	4.6 (8)	C19—N3—Cu1—O1	−6.0 (5)
C1—C6—C12—C13	−177.6 (5)	C20—N3—Cu1—O1	179.6 (5)
N1—C16—C17—C18i	−63.0 (6)	C19—N3—Cu1—N1	91.6 (7)
N3—C20—C21—N2	0.3 (7)	C20—N3—Cu1—N1	−82.9 (7)
C2—C7—N1—C16	179.6 (5)	C19—N3—Cu1—O2	−172.2 (5)
C2—C7—N1—Cu1	0.8 (7)	C20—N3—Cu1—O2	13.3 (5)
C17—C16—N1—C7	116.9 (5)

Table 1

Selected bond lengths (Å)

N1—Cu1	1.957 (4)
N3—Cu1	1.989 (4)
O1—Cu1	1.910 (3)
O2—Cu1	1.966 (3)