Tetra-μ-acetato-κ8O:O′-bis­[(2-phen­oxy­pyrimidine-κN1)copper(II)](Cu—Cu)

Fairuz, Z.A.; Abdullah, Z.; Nasir, S.B.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811044345

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1637

doi:10.1107/S1600536811044345

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Tetra-μ-acetato-κ⁸O:O′-bis[(2-phenoxypyrimidine-κN¹)copper(II)](Cu—Cu)

Zainal Abidin Fairuz,^a Zanariah Abdullah,^a ‡ Shah Bakhtiar Nasir,^a Seik Weng Ng ^a,^b and Edward R. T. Tiekink ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 24 October 2011; accepted 25 October 2011; online 29 October 2011)

The complete dinuclear molecule of the title complex, [Cu₂(CH₃COO)₄(C₁₀H₈N₂O)₂], is generated by a centre of inversion. The Cu^II atom is in a distorted octahedral coordination geometry defined by four O atoms derived from four bridging acetate ligands, a terminally connected pyrimidine N atom and a Cu atom.

Related literature

For structures of related examples of tetrakisacetatobis[(N-donor)copper] complexes, see: Fairuz et al. (2010a ,b ).

Experimental

Crystal data

[Cu₂(C₂H₃O₂)₄(C₁₀H₈N₂O)₂]
M_r = 707.64
Monoclinic, P 2₁ /n
a = 11.0738 (9) Å
b = 7.5002 (6) Å
c = 18.0539 (14) Å
β = 100.579 (1)°
V = 1474.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.51 mm⁻¹
T = 100 K
0.25 × 0.24 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.637, T_max = 0.746
11124 measured reflections
2581 independent reflections
2249 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.175
S = 1.08
2581 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 1.83 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O3	1.954 (4)
Cu1—O1	1.966 (4)
Cu1—O4ⁱ	1.977 (3)
Cu1—O2ⁱ	1.979 (4)
Cu1—N1	2.207 (4)
Cu1—Cu1ⁱ	2.6154 (10)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811044345/hg5123sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044345/hg5123Isup2.hkl

checkCIF report

Comment top

It was in connection with recent structural studies of tetrakisacetatobis[(N-donor)copper(II)] complexes (Fairuz et al., 2010a; Fairuz et al., 2010b), that the crystal structure of the title complex, (I), was investigated. The complex, Fig. 1, is centrosymmetric and features four symmetrically bridging acetate ligands and two terminally connected N atoms from the 2-phenoxypyrimidine ligands, Table 1. The Cu—Cu distance is 2.6154 (10) Å. The resulting CuNO₄ donor set defines a distorted octahedral geometry. The 2-phenoxypyrimidine ligand is twisted with the dihedral angle between the pyrimidyl and benzene rings being 63.3 (3)°.

Related literature top

For structures of related examples of tetrakisacetatobis[(N-donor)copper] complexes, see: Fairuz et al. (2010a,b).

Experimental top

2-Phenoxypyrimidine (1.1 mmol) was dissolved in acetonitrile (15 ml), added to trimethyl orthoformate (10 ml) and the mixture then heated to 50°C. Copper acetate (0.5 mmol) dissolved in acetonitrile (15 ml) was added to the solution. The green precipitate that formed was collected and recrystallized from acetonitrile to give green crystals.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. The complex is centrosymmetric. The unlabelled atoms are related by the symmetry operation 1 - x, 1 - y, 1 - z.

Tetra-µ-acetato-κ⁸O:O'-bis[(2- phenoxypyrimidine-κN¹)copper(II)](Cu—Cu) top

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₁₀H₈N₂O)₂]	F(000) = 724
M_r = 707.64	D_x = 1.594 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3884 reflections
a = 11.0738 (9) Å	θ = 2.3–27.1°
b = 7.5002 (6) Å	µ = 1.51 mm⁻¹
c = 18.0539 (14) Å	T = 100 K
β = 100.579 (1)°	Plate, green
V = 1474.0 (2) Å³	0.25 × 0.24 × 0.04 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	2581 independent reflections
Radiation source: fine-focus sealed tube	2249 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.637, T_max = 0.746	k = −8→8
11124 measured reflections	l = −21→21

Refinement top

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.1094P)² + 3.359P] where P = (F_o² + 2F_c²)/3
2581 reflections	(Δ/σ)_max = 0.001
201 parameters	Δρ_max = 1.83 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₁₀H₈N₂O)₂]	V = 1474.0 (2) Å³
M_r = 707.64	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.0738 (9) Å	µ = 1.51 mm⁻¹
b = 7.5002 (6) Å	T = 100 K
c = 18.0539 (14) Å	0.25 × 0.24 × 0.04 mm
β = 100.579 (1)°

Data collection top

Bruker SMART APEX diffractometer	2581 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2249 reflections with I > 2σ(I)
T_min = 0.637, T_max = 0.746	R_int = 0.037
11124 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.08	Δρ_max = 1.83 e Å⁻³
2581 reflections	Δρ_min = −0.55 e Å⁻³
201 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.41133 (5)	0.58752 (7)	0.52267 (3)	0.0279 (3)
O1	0.3059 (3)	0.4099 (4)	0.4621 (2)	0.0415 (9)
O2	0.4556 (3)	0.2595 (5)	0.4231 (2)	0.0463 (9)
O3	0.4384 (4)	0.4244 (5)	0.6085 (2)	0.0479 (10)
O4	0.5873 (3)	0.2712 (5)	0.5697 (2)	0.0421 (9)
O5	0.1716 (4)	0.5271 (5)	0.5969 (3)	0.0520 (11)
N1	0.2668 (3)	0.7572 (5)	0.5552 (2)	0.0304 (8)
N2	0.0888 (4)	0.8062 (6)	0.6078 (3)	0.0436 (11)
C1	0.5176 (4)	0.3045 (6)	0.6154 (3)	0.0326 (10)
C2	0.5298 (7)	0.1861 (9)	0.6841 (3)	0.0597 (17)
H2A	0.6101	0.2059	0.7163	0.090*
H2B	0.5228	0.0609	0.6683	0.090*
H2C	0.4646	0.2146	0.7122	0.090*
C3	0.3455 (5)	0.2911 (6)	0.4241 (3)	0.0331 (10)
C4	0.2508 (5)	0.1755 (8)	0.3750 (3)	0.0484 (14)
H4A	0.2681	0.0497	0.3872	0.073*
H4B	0.2545	0.1964	0.3218	0.073*
H4C	0.1687	0.2056	0.3841	0.073*
C5	0.1732 (4)	0.7050 (6)	0.5869 (3)	0.0316 (10)
C6	0.2763 (5)	0.9324 (7)	0.5446 (3)	0.0413 (13)
H6	0.3425	0.9762	0.5231	0.050*
C7	0.1930 (6)	1.0506 (8)	0.5640 (4)	0.0546 (16)
H7	0.1998	1.1753	0.5565	0.065*
C8	0.0997 (6)	0.9796 (8)	0.5947 (4)	0.0565 (16)
H8	0.0394	1.0582	0.6075	0.068*
C9	0.0924 (5)	0.4472 (6)	0.6393 (3)	0.0374 (12)
C10	0.1489 (5)	0.3652 (9)	0.7058 (3)	0.0515 (14)
H10	0.2348	0.3764	0.7234	0.062*
C11	0.0762 (6)	0.2666 (9)	0.7457 (3)	0.0567 (16)
H11	0.1127	0.2093	0.7913	0.068*
C12	−0.0480 (6)	0.2509 (8)	0.7200 (3)	0.0487 (14)
H12	−0.0970	0.1818	0.7473	0.058*
C13	−0.1003 (5)	0.3352 (8)	0.6553 (3)	0.0461 (13)
H13	−0.1864	0.3255	0.6383	0.055*
C14	−0.0313 (5)	0.4344 (7)	0.6136 (3)	0.0405 (12)
H14	−0.0690	0.4921	0.5684	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0235 (4)	0.0277 (4)	0.0343 (4)	0.0048 (2)	0.0105 (2)	0.0017 (2)
O1	0.0300 (19)	0.040 (2)	0.054 (2)	0.0005 (14)	0.0077 (17)	−0.0082 (16)
O2	0.0293 (18)	0.048 (2)	0.062 (2)	−0.0022 (16)	0.0099 (16)	−0.0188 (19)
O3	0.052 (2)	0.052 (2)	0.044 (2)	0.0165 (18)	0.0223 (19)	0.0130 (17)
O4	0.043 (2)	0.0395 (19)	0.049 (2)	0.0127 (16)	0.0212 (17)	0.0127 (16)
O5	0.046 (2)	0.0279 (18)	0.094 (3)	0.0067 (16)	0.045 (2)	0.0048 (19)
N1	0.0276 (19)	0.0273 (19)	0.039 (2)	0.0041 (15)	0.0134 (16)	0.0005 (17)
N2	0.039 (2)	0.033 (2)	0.064 (3)	0.0047 (18)	0.025 (2)	−0.006 (2)
C1	0.032 (2)	0.031 (2)	0.035 (2)	−0.005 (2)	0.005 (2)	0.0059 (19)
C2	0.067 (4)	0.064 (4)	0.049 (3)	0.010 (3)	0.013 (3)	0.026 (3)
C3	0.035 (3)	0.033 (2)	0.031 (2)	−0.002 (2)	0.005 (2)	0.0073 (19)
C4	0.040 (3)	0.048 (3)	0.055 (3)	−0.008 (2)	0.002 (3)	−0.006 (3)
C5	0.025 (2)	0.029 (2)	0.042 (3)	0.0016 (18)	0.0096 (19)	−0.0058 (19)
C6	0.038 (3)	0.035 (3)	0.055 (3)	0.002 (2)	0.020 (3)	0.001 (2)
C7	0.068 (4)	0.031 (3)	0.072 (4)	0.007 (3)	0.033 (3)	0.001 (3)
C8	0.059 (4)	0.032 (3)	0.089 (5)	0.013 (3)	0.041 (3)	−0.007 (3)
C9	0.035 (3)	0.028 (2)	0.054 (3)	0.002 (2)	0.023 (2)	−0.004 (2)
C10	0.036 (3)	0.058 (3)	0.055 (4)	0.002 (3)	−0.006 (3)	−0.007 (3)
C11	0.074 (4)	0.058 (4)	0.037 (3)	0.006 (3)	0.007 (3)	0.004 (3)
C12	0.055 (3)	0.044 (3)	0.055 (3)	0.001 (3)	0.032 (3)	0.001 (3)
C13	0.028 (3)	0.047 (3)	0.067 (4)	0.004 (2)	0.019 (2)	−0.003 (3)
C14	0.035 (3)	0.040 (3)	0.045 (3)	0.007 (2)	0.004 (2)	0.003 (2)

Geometric parameters (Å, º) top

Cu1—O3	1.954 (4)	C2—H2C	0.9800
Cu1—O1	1.966 (4)	C3—C4	1.515 (7)
Cu1—O4ⁱ	1.977 (3)	C4—H4A	0.9800
Cu1—O2ⁱ	1.979 (4)	C4—H4B	0.9800
Cu1—N1	2.207 (4)	C4—H4C	0.9800
Cu1—Cu1ⁱ	2.6154 (10)	C6—C7	1.371 (8)
O1—C3	1.252 (6)	C6—H6	0.9500
O2—C3	1.246 (6)	C7—C8	1.367 (9)
O2—Cu1ⁱ	1.979 (4)	C7—H7	0.9500
O3—C1	1.246 (6)	C8—H8	0.9500
O4—C1	1.254 (6)	C9—C14	1.367 (8)
O4—Cu1ⁱ	1.977 (3)	C9—C10	1.391 (8)
O5—C5	1.347 (6)	C10—C11	1.389 (9)
O5—C9	1.400 (6)	C10—H10	0.9500
N1—C5	1.331 (6)	C11—C12	1.373 (9)
N1—C6	1.335 (6)	C11—H11	0.9500
N2—C5	1.312 (6)	C12—C13	1.361 (8)
N2—C8	1.331 (8)	C12—H12	0.9500
C1—C2	1.511 (7)	C13—C14	1.383 (8)
C2—H2A	0.9800	C13—H13	0.9500
C2—H2B	0.9800	C14—H14	0.9500

O3—Cu1—O1	90.30 (18)	C3—C4—H4A	109.5
O3—Cu1—O4ⁱ	168.58 (15)	C3—C4—H4B	109.5
O1—Cu1—O4ⁱ	89.46 (16)	H4A—C4—H4B	109.5
O3—Cu1—O2ⁱ	88.77 (18)	C3—C4—H4C	109.5
O1—Cu1—O2ⁱ	168.63 (15)	H4A—C4—H4C	109.5
O4ⁱ—Cu1—O2ⁱ	89.22 (17)	H4B—C4—H4C	109.5
O3—Cu1—N1	99.39 (15)	N2—C5—N1	127.3 (4)
O1—Cu1—N1	98.78 (15)	N2—C5—O5	120.4 (4)
O4ⁱ—Cu1—N1	91.93 (14)	N1—C5—O5	112.3 (4)
O2ⁱ—Cu1—N1	92.55 (14)	N1—C6—C7	121.7 (5)
O3—Cu1—Cu1ⁱ	85.37 (11)	N1—C6—H6	119.1
O1—Cu1—Cu1ⁱ	83.66 (11)	C7—C6—H6	119.1
O4ⁱ—Cu1—Cu1ⁱ	83.26 (10)	C8—C7—C6	116.5 (5)
O2ⁱ—Cu1—Cu1ⁱ	84.97 (11)	C8—C7—H7	121.8
N1—Cu1—Cu1ⁱ	174.60 (11)	C6—C7—H7	121.8
C3—O1—Cu1	123.7 (3)	N2—C8—C7	123.5 (5)
C3—O2—Cu1ⁱ	121.6 (3)	N2—C8—H8	118.2
C1—O3—Cu1	122.2 (3)	C7—C8—H8	118.2
C1—O4—Cu1ⁱ	123.3 (3)	C14—C9—C10	121.7 (5)
C5—O5—C9	121.5 (4)	C14—C9—O5	122.3 (5)
C5—N1—C6	116.0 (4)	C10—C9—O5	115.7 (5)
C5—N1—Cu1	127.2 (3)	C11—C10—C9	118.1 (5)
C6—N1—Cu1	116.7 (3)	C11—C10—H10	120.9
C5—N2—C8	114.9 (5)	C9—C10—H10	120.9
O3—C1—O4	125.8 (4)	C12—C11—C10	120.7 (5)
O3—C1—C2	117.5 (5)	C12—C11—H11	119.6
O4—C1—C2	116.7 (5)	C10—C11—H11	119.6
C1—C2—H2A	109.5	C13—C12—C11	119.5 (5)
C1—C2—H2B	109.5	C13—C12—H12	120.3
H2A—C2—H2B	109.5	C11—C12—H12	120.3
C1—C2—H2C	109.5	C12—C13—C14	121.8 (5)
H2A—C2—H2C	109.5	C12—C13—H13	119.1
H2B—C2—H2C	109.5	C14—C13—H13	119.1
O2—C3—O1	125.9 (5)	C9—C14—C13	118.2 (5)
O2—C3—C4	117.1 (5)	C9—C14—H14	120.9
O1—C3—C4	117.0 (5)	C13—C14—H14	120.9

O3—Cu1—O1—C3	−87.8 (4)	Cu1—O1—C3—C4	−174.5 (4)
O4ⁱ—Cu1—O1—C3	80.8 (4)	C8—N2—C5—N1	0.3 (8)
O2ⁱ—Cu1—O1—C3	−2.6 (11)	C8—N2—C5—O5	−179.7 (6)
N1—Cu1—O1—C3	172.6 (4)	C6—N1—C5—N2	1.1 (8)
Cu1ⁱ—Cu1—O1—C3	−2.5 (4)	Cu1—N1—C5—N2	178.4 (4)
O1—Cu1—O3—C1	83.2 (4)	C6—N1—C5—O5	−178.8 (5)
O4ⁱ—Cu1—O3—C1	−5.6 (11)	Cu1—N1—C5—O5	−1.5 (6)
O2ⁱ—Cu1—O3—C1	−85.5 (4)	C9—O5—C5—N2	−9.6 (8)
N1—Cu1—O3—C1	−177.9 (4)	C9—O5—C5—N1	170.4 (5)
Cu1ⁱ—Cu1—O3—C1	−0.5 (4)	C5—N1—C6—C7	−1.2 (8)
O3—Cu1—N1—C5	−39.5 (4)	Cu1—N1—C6—C7	−178.8 (5)
O1—Cu1—N1—C5	52.2 (4)	N1—C6—C7—C8	0.0 (10)
O4ⁱ—Cu1—N1—C5	142.0 (4)	C5—N2—C8—C7	−1.8 (10)
O2ⁱ—Cu1—N1—C5	−128.7 (4)	C6—C7—C8—N2	1.7 (11)
O3—Cu1—N1—C6	137.7 (4)	C5—O5—C9—C14	72.4 (7)
O1—Cu1—N1—C6	−130.5 (4)	C5—O5—C9—C10	−114.0 (6)
O4ⁱ—Cu1—N1—C6	−40.8 (4)	C14—C9—C10—C11	0.9 (9)
O2ⁱ—Cu1—N1—C6	48.5 (4)	O5—C9—C10—C11	−172.8 (5)
Cu1—O3—C1—O4	−1.0 (8)	C9—C10—C11—C12	−0.1 (9)
Cu1—O3—C1—C2	−179.8 (4)	C10—C11—C12—C13	−0.9 (9)
Cu1ⁱ—O4—C1—O3	2.4 (7)	C11—C12—C13—C14	1.1 (9)
Cu1ⁱ—O4—C1—C2	−178.7 (4)	C10—C9—C14—C13	−0.7 (8)
Cu1ⁱ—O2—C3—O1	−5.4 (7)	O5—C9—C14—C13	172.5 (5)
Cu1ⁱ—O2—C3—C4	174.6 (4)	C12—C13—C14—C9	−0.3 (8)
Cu1—O1—C3—O2	5.5 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₂H₃O₂)₄(C₁₀H₈N₂O)₂]
M_r	707.64
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	11.0738 (9), 7.5002 (6), 18.0539 (14)
β (°)	100.579 (1)
V (Å³)	1474.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.51
Crystal size (mm)	0.25 × 0.24 × 0.04

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.637, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	11124, 2581, 2249
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.175, 1.08
No. of reflections	2581
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.83, −0.55

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu1—O3	1.954 (4)	Cu1—O2ⁱ	1.979 (4)
Cu1—O1	1.966 (4)	Cu1—N1	2.207 (4)
Cu1—O4ⁱ	1.977 (3)	Cu1—Cu1ⁱ	2.6154 (10)

Symmetry code: (i) −x+1, −y+1, −z+1.

Footnotes

‡Additional correspondence author, e-mail: zana@um.edu.my.

Acknowledgements

We thank the University of Malaya (grant No. RG027/09AFR) for supporting this study.

References

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