Tetra-μ-acetato-κ8O:O′-bis­{[4-methyl-2-(m-tolyl­amino)pyridine-κN]copper(II)}

Fairuz, Z.A.; Aiyub, Z.; Abdullah, Z.; Ng, S.W.

doi:10.1107/S1600536809055858

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page m165

https://doi.org/10.1107/S1600536809055858

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Tetra-μ-acetato-κ⁸O:O′-bis{[4-methyl-2-(m-tolylamino)pyridine-κN]copper(II)}

Zainal Abidin Fairuz,^a Zaharah Aiyub,^a Zanariah Abdullah ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 12 December 2009; accepted 30 December 2009; online 16 January 2010)

In the crystal structure of the title binuclear complex, [Cu₂(CH₃COO)₄(C₁₃H₁₄N₂)₂], the four acetate groups each bridge a pair of Cu^II atoms. The coordination of the metal atoms is distorted square-pyramidal, with the bonding O atoms comprising a square basal plane and the coordinating N atom of the N-heterocycle occupying the apical position. In the two N-hetercycle ligands, the benzene rings are twisted with respect to the pyridine rings, making dihedral angles of 53.1 (2) and 54.2 (2)°. Intramolecular N—H⋯O hydrogen bonding is present between the imino and carboxy groups. The crystal studied was a non-merohedral twin with a minor twin component of 21.4%.

Related literature

For the 2-(m-tolylamino)pyridine adduct, see: Fairuz et al. (2009 ). For the treatment of diffraction data of twinned crystals, see: Spek (2003 ).

Experimental

Crystal data

[Cu₂(C₂H₃O₂)₄(C₁₃H₁₄N₂)₂]
M_r = 759.78
Triclinic, $[P \overline 1]$
a = 8.2489 (4) Å
b = 14.2110 (7) Å
c = 16.4484 (8) Å
α = 107.798 (1)°
β = 101.971 (1)°
γ = 97.661 (1)°
V = 1755.45 (15) Å³
Z = 2
Mo Kα radiation
μ = 1.27 mm⁻¹
T = 295 K
0.40 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.631, T_max = 0.884
21605 measured reflections
7963 independent reflections
6719 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.231
S = 1.12
7963 reflections
442 parameters
H-atom parameters constrained
Δρ_max = 1.01 e Å⁻³
Δρ_min = −0.91 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.985 (4)
Cu1—O4	1.961 (5)
Cu1—O6	1.963 (4)
Cu1—O8	1.956 (5)
Cu1—N1	2.215 (5)
Cu1—Cu	2.6576 (9)
Cu2—O2	1.968 (4)
Cu2—O3	2.001 (5)
Cu2—O5	1.957 (5)
Cu2—O7	1.981 (5)
Cu2—N3	2.208 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.99	2.830 (6)	165
N4—H4⋯O3	0.86	2.18	2.964 (8)	152

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809055858/xu2709sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055858/xu2709Isup2.hkl

checkCIF report

Related literature top

For the 2-(m-tolylamino)pyridine adduct, see: Fairuz et al. (2009). For the treatment of twinned diffraction data, see: Spek (2003).

Experimental top

Copper acetate (0.1 g, 0.5 mmol) was dissolved in acetonitrile (5 ml). The solution was mixed with a solution of 4-methyl-2-(m-tolylamino)pyridine (0.2 g, 1.1 mmol) dissolved in acetonitrile (15 ml). The green precipitate that formed was recrystallized from acetonitrile to give greenish-blue crystals.

Structure description top

For the 2-(m-tolylamino)pyridine adduct, see: Fairuz et al. (2009). For the treatment of twinned diffraction data, see: Spek (2003).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Cu₂(C₂H₃O₂)₂(C₁₃H₁₄N₂)₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Tetra-µ-acetato-κ⁸O:O'-bis{[4-methyl-2-(m- tolylamino)pyridine-κN]copper(II)} top

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₁₃H₁₄N₂)₂]	Z = 2
M_r = 759.78	F(000) = 788
Triclinic, P1	D_x = 1.437 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2489 (4) Å	Cell parameters from 9994 reflections
b = 14.2110 (7) Å	θ = 2.4–28.3°
c = 16.4484 (8) Å	µ = 1.27 mm⁻¹
α = 107.798 (1)°	T = 295 K
β = 101.971 (1)°	Prism, blue
γ = 97.661 (1)°	0.40 × 0.10 × 0.10 mm
V = 1755.45 (15) Å³

Data collection top

Bruker SMART APEX diffractometer	7963 independent reflections
Radiation source: fine-focus sealed tube	6719 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 27.5°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.631, T_max = 0.884	k = −18→18
21605 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.231	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0917P)² + 6.9746P] where P = (F_o² + 2F_c²)/3
7963 reflections	(Δ/σ)_max = 0.001
442 parameters	Δρ_max = 1.01 e Å⁻³
0 restraints	Δρ_min = −0.91 e Å⁻³

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₁₃H₁₄N₂)₂]	γ = 97.661 (1)°
M_r = 759.78	V = 1755.45 (15) Å³
Triclinic, P1	Z = 2
a = 8.2489 (4) Å	Mo Kα radiation
b = 14.2110 (7) Å	µ = 1.27 mm⁻¹
c = 16.4484 (8) Å	T = 295 K
α = 107.798 (1)°	0.40 × 0.10 × 0.10 mm
β = 101.971 (1)°

Data collection top

Bruker SMART APEX diffractometer	7963 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6719 reflections with I > 2σ(I)
T_min = 0.631, T_max = 0.884	R_int = 0.030
21605 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.231	H-atom parameters constrained
S = 1.12	Δρ_max = 1.01 e Å⁻³
7963 reflections	Δρ_min = −0.91 e Å⁻³
442 parameters

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

	x	y	z	U_iso*/U_eq
Cu1	0.86052 (8)	0.69737 (5)	0.46112 (4)	0.03279 (19)
Cu2	0.79744 (9)	0.63662 (5)	0.28585 (4)	0.0358 (2)
N1	0.9016 (6)	0.7346 (4)	0.6058 (3)	0.0375 (10)
N2	0.6928 (7)	0.8250 (4)	0.6207 (3)	0.0477 (13)
H2	0.6773	0.8115	0.5647	0.057*
N3	0.7634 (7)	0.5752 (4)	0.1414 (3)	0.0446 (12)
N4	0.7788 (10)	0.7301 (4)	0.1219 (4)	0.0630 (18)
H4	0.7981	0.7548	0.1785	0.076*
O1	0.6452 (6)	0.7438 (4)	0.4354 (3)	0.0503 (11)
O2	0.6044 (6)	0.7040 (4)	0.2906 (3)	0.0508 (11)
O3	0.9404 (6)	0.7729 (4)	0.3116 (3)	0.0502 (11)
O4	0.9801 (6)	0.8244 (3)	0.4577 (3)	0.0503 (11)
O5	1.0020 (6)	0.5821 (4)	0.3059 (3)	0.0494 (11)
O6	1.0653 (6)	0.6426 (4)	0.4532 (3)	0.0515 (12)
O7	0.6626 (6)	0.5144 (4)	0.2927 (3)	0.0528 (12)
O8	0.7303 (6)	0.5625 (4)	0.4395 (3)	0.0515 (11)
C1	0.5674 (8)	0.7429 (5)	0.3606 (4)	0.0399 (12)
C2	0.4178 (10)	0.7926 (6)	0.3580 (5)	0.0582 (19)
H2A	0.3212	0.7470	0.3134	0.087*
H2B	0.4435	0.8530	0.3442	0.087*
H2C	0.3930	0.8096	0.4146	0.087*
C3	0.9957 (7)	0.8375 (4)	0.3880 (4)	0.0403 (13)
C4	1.0904 (10)	0.9404 (5)	0.3968 (6)	0.0580 (18)
H4A	1.1758	0.9680	0.4522	0.087*
H4B	1.0124	0.9847	0.3948	0.087*
H4C	1.1430	0.9339	0.3491	0.087*
C5	1.0947 (7)	0.5954 (5)	0.3810 (4)	0.0400 (12)
C6	1.2513 (9)	0.5518 (6)	0.3873 (5)	0.0572 (18)
H6A	1.3469	0.6033	0.4267	0.086*
H6B	1.2708	0.5273	0.3297	0.086*
H6C	1.2362	0.4971	0.4096	0.086*
C7	0.6589 (8)	0.5004 (5)	0.3637 (5)	0.0437 (14)
C8	0.5583 (10)	0.4005 (5)	0.3577 (6)	0.0594 (19)
H8A	0.5146	0.4097	0.4087	0.089*
H8B	0.6304	0.3526	0.3554	0.089*
H8C	0.4658	0.3758	0.3051	0.089*
C9	1.0151 (8)	0.6885 (5)	0.6409 (4)	0.0458 (14)
H9	1.0743	0.6525	0.6042	0.055*
C10	1.0498 (8)	0.6906 (5)	0.7262 (4)	0.0474 (15)
H10	1.1312	0.6579	0.7466	0.057*
C11	0.9612 (8)	0.7425 (5)	0.7821 (4)	0.0416 (13)
C12	0.8430 (8)	0.7908 (5)	0.7484 (4)	0.0402 (13)
H12	0.7829	0.8269	0.7845	0.048*
C13	0.8138 (7)	0.7852 (4)	0.6601 (4)	0.0331 (11)
C14	0.9903 (11)	0.7440 (7)	0.8763 (5)	0.063 (2)
H14A	0.8965	0.7633	0.8987	0.095*
H14B	1.0929	0.7918	0.9123	0.095*
H14C	0.9999	0.6779	0.8777	0.095*
C15	0.5887 (8)	0.8861 (5)	0.6609 (4)	0.0404 (13)
C16	0.6562 (9)	0.9697 (5)	0.7366 (4)	0.0438 (13)
H16	0.7715	0.9842	0.7644	0.053*
C17	0.5539 (10)	1.0326 (5)	0.7719 (4)	0.0511 (16)
C18	0.3834 (11)	1.0100 (7)	0.7289 (6)	0.066 (2)
H18	0.3136	1.0516	0.7515	0.079*
C19	0.3146 (11)	0.9265 (7)	0.6527 (7)	0.072 (2)
H19	0.1999	0.9125	0.6239	0.086*
C20	0.4190 (9)	0.8643 (6)	0.6201 (5)	0.0518 (16)
H20	0.3733	0.8070	0.5699	0.062*
C21	0.6282 (15)	1.1255 (7)	0.8540 (6)	0.080 (3)
H21A	0.5907	1.1829	0.8436	0.120*
H21B	0.7497	1.1377	0.8678	0.120*
H21C	0.5912	1.1148	0.9027	0.120*
C22	0.7531 (11)	0.4764 (5)	0.1082 (4)	0.0535 (17)
H22	0.7495	0.4395	0.1460	0.064*
C23	0.7473 (11)	0.4248 (5)	0.0217 (5)	0.0571 (18)
H23	0.7372	0.3551	0.0019	0.068*
C24	0.7568 (9)	0.4778 (5)	−0.0355 (4)	0.0495 (15)
C25	0.7643 (11)	0.5799 (6)	−0.0030 (5)	0.0568 (18)
H25	0.7676	0.6179	−0.0399	0.068*
C26	0.7669 (9)	0.6269 (5)	0.0855 (4)	0.0461 (14)
C27	0.7588 (13)	0.4265 (6)	−0.1297 (5)	0.069 (2)
H27A	0.7902	0.3625	−0.1358	0.104*
H27B	0.8394	0.4683	−0.1454	0.104*
H27C	0.6480	0.4159	−0.1681	0.104*
C28	0.7628 (9)	0.7992 (5)	0.0763 (4)	0.0479 (15)
C29	0.6370 (9)	0.7780 (6)	0.0001 (5)	0.0509 (16)
H29	0.5640	0.7149	−0.0241	0.061*
C30	0.6161 (10)	0.8499 (6)	−0.0424 (5)	0.0590 (18)
C31	0.7265 (13)	0.9410 (7)	−0.0052 (7)	0.075 (2)
H31	0.7166	0.9898	−0.0318	0.090*
C32	0.8540 (15)	0.9624 (7)	0.0719 (7)	0.085 (3)
H32	0.9281	1.0252	0.0962	0.102*
C33	0.8715 (10)	0.8916 (6)	0.1122 (5)	0.0600 (19)
H33	0.9569	0.9064	0.1638	0.072*
C34	0.4771 (12)	0.8248 (9)	−0.1222 (6)	0.083 (3)
H34A	0.5157	0.8512	−0.1636	0.124*
H34B	0.3845	0.8540	−0.1068	0.124*
H34C	0.4400	0.7527	−0.1485	0.124*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0316 (3)	0.0375 (4)	0.0286 (3)	0.0092 (3)	0.0081 (3)	0.0095 (3)
Cu2	0.0371 (4)	0.0404 (4)	0.0286 (3)	0.0096 (3)	0.0090 (3)	0.0092 (3)
N1	0.040 (3)	0.043 (3)	0.031 (2)	0.015 (2)	0.0123 (19)	0.009 (2)
N2	0.060 (3)	0.060 (3)	0.028 (2)	0.035 (3)	0.016 (2)	0.010 (2)
N3	0.057 (3)	0.046 (3)	0.031 (2)	0.014 (2)	0.008 (2)	0.013 (2)
N4	0.111 (6)	0.044 (3)	0.033 (3)	0.016 (3)	0.017 (3)	0.013 (2)
O1	0.050 (3)	0.071 (3)	0.035 (2)	0.029 (2)	0.0111 (19)	0.018 (2)
O2	0.042 (2)	0.073 (3)	0.039 (2)	0.025 (2)	0.0098 (19)	0.017 (2)
O3	0.057 (3)	0.046 (2)	0.045 (3)	0.003 (2)	0.016 (2)	0.014 (2)
O4	0.060 (3)	0.042 (2)	0.043 (2)	0.000 (2)	0.012 (2)	0.0105 (19)
O5	0.050 (3)	0.062 (3)	0.043 (2)	0.026 (2)	0.019 (2)	0.017 (2)
O6	0.044 (2)	0.075 (3)	0.040 (2)	0.029 (2)	0.0148 (19)	0.016 (2)
O7	0.057 (3)	0.046 (3)	0.046 (3)	−0.001 (2)	0.016 (2)	0.007 (2)
O8	0.058 (3)	0.047 (3)	0.044 (2)	0.000 (2)	0.008 (2)	0.017 (2)
C1	0.037 (3)	0.044 (3)	0.043 (3)	0.014 (2)	0.012 (2)	0.019 (3)
C2	0.055 (4)	0.076 (5)	0.061 (4)	0.038 (4)	0.021 (3)	0.034 (4)
C3	0.034 (3)	0.037 (3)	0.052 (4)	0.008 (2)	0.015 (3)	0.016 (3)
C4	0.059 (4)	0.046 (4)	0.073 (5)	0.004 (3)	0.028 (4)	0.023 (3)
C5	0.035 (3)	0.040 (3)	0.047 (3)	0.008 (2)	0.013 (3)	0.017 (3)
C6	0.045 (4)	0.069 (5)	0.066 (5)	0.025 (3)	0.021 (3)	0.026 (4)
C7	0.032 (3)	0.038 (3)	0.059 (4)	0.007 (2)	0.014 (3)	0.013 (3)
C8	0.054 (4)	0.039 (3)	0.082 (5)	0.005 (3)	0.022 (4)	0.015 (3)
C9	0.045 (3)	0.062 (4)	0.036 (3)	0.024 (3)	0.014 (3)	0.017 (3)
C10	0.046 (3)	0.065 (4)	0.037 (3)	0.024 (3)	0.008 (3)	0.021 (3)
C11	0.043 (3)	0.050 (3)	0.037 (3)	0.011 (3)	0.014 (2)	0.020 (3)
C12	0.047 (3)	0.048 (3)	0.030 (3)	0.016 (3)	0.013 (2)	0.015 (2)
C13	0.035 (3)	0.035 (3)	0.030 (3)	0.008 (2)	0.011 (2)	0.009 (2)
C14	0.077 (5)	0.090 (6)	0.047 (4)	0.038 (5)	0.028 (4)	0.040 (4)
C15	0.045 (3)	0.041 (3)	0.040 (3)	0.016 (3)	0.018 (3)	0.014 (2)
C16	0.050 (4)	0.044 (3)	0.043 (3)	0.014 (3)	0.017 (3)	0.017 (3)
C17	0.071 (5)	0.047 (4)	0.042 (3)	0.023 (3)	0.027 (3)	0.014 (3)
C18	0.060 (5)	0.074 (5)	0.075 (5)	0.035 (4)	0.033 (4)	0.021 (4)
C19	0.045 (4)	0.086 (6)	0.086 (6)	0.031 (4)	0.021 (4)	0.023 (5)
C20	0.046 (4)	0.055 (4)	0.053 (4)	0.020 (3)	0.013 (3)	0.014 (3)
C21	0.117 (8)	0.058 (5)	0.057 (5)	0.031 (5)	0.024 (5)	0.002 (4)
C22	0.082 (5)	0.046 (4)	0.037 (3)	0.017 (3)	0.019 (3)	0.018 (3)
C23	0.083 (5)	0.036 (3)	0.045 (4)	0.008 (3)	0.017 (4)	0.006 (3)
C24	0.058 (4)	0.046 (3)	0.035 (3)	0.007 (3)	0.014 (3)	0.002 (3)
C25	0.085 (5)	0.052 (4)	0.037 (3)	0.013 (4)	0.023 (3)	0.017 (3)
C26	0.058 (4)	0.044 (3)	0.035 (3)	0.005 (3)	0.011 (3)	0.014 (3)
C27	0.098 (7)	0.063 (5)	0.040 (4)	0.014 (4)	0.027 (4)	0.004 (3)
C28	0.060 (4)	0.043 (3)	0.044 (3)	0.012 (3)	0.019 (3)	0.016 (3)
C29	0.051 (4)	0.057 (4)	0.044 (3)	0.002 (3)	0.013 (3)	0.020 (3)
C30	0.058 (4)	0.073 (5)	0.063 (5)	0.022 (4)	0.032 (4)	0.034 (4)
C31	0.099 (7)	0.058 (5)	0.080 (6)	0.018 (5)	0.025 (5)	0.039 (5)
C32	0.108 (8)	0.053 (5)	0.085 (7)	−0.006 (5)	0.011 (6)	0.031 (5)
C33	0.060 (4)	0.054 (4)	0.056 (4)	0.001 (3)	0.005 (3)	0.016 (3)
C34	0.065 (5)	0.130 (9)	0.066 (5)	0.033 (6)	0.019 (4)	0.045 (6)

Geometric parameters (Å, º) top

Cu1—O1	1.985 (4)	C10—H10	0.9300
Cu1—O4	1.961 (5)	C11—C12	1.384 (8)
Cu1—O6	1.963 (4)	C11—C14	1.511 (9)
Cu1—O8	1.956 (5)	C12—C13	1.398 (8)
Cu1—N1	2.215 (5)	C12—H12	0.9300
Cu1—Cu2	2.6576 (9)	C14—H14A	0.9600
Cu2—O2	1.968 (4)	C14—H14B	0.9600
Cu2—O3	2.001 (5)	C14—H14C	0.9600
Cu2—O5	1.957 (5)	C15—C20	1.369 (9)
Cu2—O7	1.981 (5)	C15—C16	1.380 (9)
Cu2—N3	2.208 (5)	C16—C17	1.391 (9)
N1—C9	1.345 (8)	C16—H16	0.9300
N1—C13	1.362 (7)	C17—C18	1.382 (11)
N2—C13	1.357 (7)	C17—C21	1.515 (10)
N2—C15	1.418 (7)	C18—C19	1.384 (12)
N2—H2	0.8600	C18—H18	0.9300
N3—C26	1.344 (8)	C19—C20	1.384 (10)
N3—C22	1.325 (9)	C19—H19	0.9300
N4—C26	1.386 (9)	C20—H20	0.9300
N4—C28	1.409 (9)	C21—H21A	0.9600
N4—H4	0.8600	C21—H21B	0.9600
O1—C1	1.259 (7)	C21—H21C	0.9600
O2—C1	1.236 (7)	C22—C23	1.376 (9)
O3—C3	1.255 (8)	C22—H22	0.9300
O4—C3	1.245 (8)	C23—C24	1.379 (10)
O5—C5	1.254 (8)	C23—H23	0.9300
O6—C5	1.262 (7)	C24—C25	1.373 (10)
O7—C7	1.248 (8)	C24—C27	1.503 (9)
O8—C7	1.251 (8)	C25—C26	1.397 (9)
C1—C2	1.501 (8)	C25—H25	0.9300
C2—H2A	0.9600	C27—H27A	0.9600
C2—H2B	0.9600	C27—H27B	0.9600
C2—H2C	0.9600	C27—H27C	0.9600
C3—C4	1.513 (9)	C28—C29	1.373 (10)
C4—H4A	0.9600	C28—C33	1.367 (10)
C4—H4B	0.9600	C29—C30	1.413 (10)
C4—H4C	0.9600	C29—H29	0.9300
C5—C6	1.503 (9)	C30—C31	1.360 (12)
C6—H6A	0.9600	C30—C34	1.464 (12)
C6—H6B	0.9600	C31—C32	1.390 (14)
C6—H6C	0.9600	C31—H31	0.9300
C7—C8	1.509 (9)	C32—C33	1.371 (12)
C8—H8A	0.9600	C32—H32	0.9300
C8—H8B	0.9600	C33—H33	0.9300
C8—H8C	0.9600	C34—H34A	0.9600
C9—C10	1.362 (9)	C34—H34B	0.9600
C9—H9	0.9300	C34—H34C	0.9600
C10—C11	1.390 (9)

O8—Cu1—O4	168.87 (19)	C10—C9—H9	117.5
O8—Cu1—O6	90.3 (2)	C9—C10—C11	118.7 (6)
O4—Cu1—O6	89.0 (2)	C9—C10—H10	120.6
O8—Cu1—O1	89.5 (2)	C11—C10—H10	120.6
O4—Cu1—O1	88.3 (2)	C10—C11—C12	118.1 (6)
O6—Cu1—O1	165.03 (19)	C10—C11—C14	120.8 (6)
O8—Cu1—N1	90.72 (19)	C12—C11—C14	121.0 (6)
O4—Cu1—N1	100.40 (19)	C11—C12—C13	120.0 (5)
O6—Cu1—N1	96.21 (18)	C11—C12—H12	120.0
O1—Cu1—N1	98.76 (18)	C13—C12—H12	120.0
O8—Cu1—Cu2	84.27 (14)	N1—C13—N2	114.9 (5)
O4—Cu1—Cu2	84.61 (14)	N1—C13—C12	121.6 (5)
O6—Cu1—Cu2	83.56 (13)	N2—C13—C12	123.5 (5)
O1—Cu1—Cu2	81.53 (13)	C11—C14—H14A	109.5
N1—Cu1—Cu2	174.98 (14)	C11—C14—H14B	109.5
O5—Cu2—O2	168.97 (19)	H14A—C14—H14B	109.5
O5—Cu2—O7	89.7 (2)	C11—C14—H14C	109.5
O2—Cu2—O7	90.7 (2)	H14A—C14—H14C	109.5
O5—Cu2—O3	90.1 (2)	H14B—C14—H14C	109.5
O2—Cu2—O3	86.8 (2)	C20—C15—C16	119.8 (6)
O7—Cu2—O3	165.6 (2)	C20—C15—N2	118.6 (6)
O5—Cu2—N3	90.5 (2)	C16—C15—N2	121.5 (6)
O2—Cu2—N3	100.4 (2)	C15—C16—C17	120.7 (7)
O7—Cu2—N3	95.3 (2)	C15—C16—H16	119.6
O3—Cu2—N3	99.0 (2)	C17—C16—H16	119.6
O5—Cu2—Cu1	83.70 (13)	C18—C17—C16	118.5 (7)
O2—Cu2—Cu1	85.41 (13)	C18—C17—C21	120.6 (7)
O7—Cu2—Cu1	82.92 (14)	C16—C17—C21	120.9 (8)
O3—Cu2—Cu1	82.78 (14)	C17—C18—C19	121.2 (7)
N3—Cu2—Cu1	173.93 (14)	C17—C18—H18	119.4
C9—N1—C13	116.6 (5)	C19—C18—H18	119.4
C9—N1—Cu1	113.6 (4)	C20—C19—C18	119.0 (8)
C13—N1—Cu1	129.2 (4)	C20—C19—H19	120.5
C13—N2—C15	127.8 (5)	C18—C19—H19	120.5
C13—N2—H2	116.1	C15—C20—C19	120.8 (7)
C15—N2—H2	116.1	C15—C20—H20	119.6
C26—N3—C22	116.8 (6)	C19—C20—H20	119.6
C26—N3—Cu2	127.7 (4)	C17—C21—H21A	109.5
C22—N3—Cu2	115.2 (4)	C17—C21—H21B	109.5
C26—N4—C28	127.2 (6)	H21A—C21—H21B	109.5
C26—N4—H4	116.4	C17—C21—H21C	109.5
C28—N4—H4	116.4	H21A—C21—H21C	109.5
C1—O1—Cu1	125.2 (4)	H21B—C21—H21C	109.5
C1—O2—Cu2	122.2 (4)	N3—C22—C23	124.4 (6)
C3—O3—Cu2	123.2 (4)	N3—C22—H22	117.8
C3—O4—Cu1	123.4 (4)	C23—C22—H22	117.8
C5—O5—Cu2	124.1 (4)	C22—C23—C24	119.2 (6)
C5—O6—Cu1	123.7 (4)	C22—C23—H23	120.4
C7—O7—Cu2	123.7 (4)	C24—C23—H23	120.4
C7—O8—Cu1	123.3 (4)	C23—C24—C25	117.4 (6)
O2—C1—O1	125.1 (6)	C23—C24—C27	121.8 (7)
O2—C1—C2	118.5 (6)	C25—C24—C27	120.8 (7)
O1—C1—C2	116.4 (6)	C24—C25—C26	120.1 (7)
C1—C2—H2A	109.5	C24—C25—H25	120.0
C1—C2—H2B	109.5	C26—C25—H25	120.0
H2A—C2—H2B	109.5	N3—C26—N4	115.7 (6)
C1—C2—H2C	109.5	N3—C26—C25	122.0 (6)
H2A—C2—H2C	109.5	N4—C26—C25	122.2 (6)
H2B—C2—H2C	109.5	C24—C27—H27A	109.5
O4—C3—O3	125.7 (6)	C24—C27—H27B	109.5
O4—C3—C4	116.8 (6)	H27A—C27—H27B	109.5
O3—C3—C4	117.5 (6)	C24—C27—H27C	109.5
C3—C4—H4A	109.5	H27A—C27—H27C	109.5
C3—C4—H4B	109.5	H27B—C27—H27C	109.5
H4A—C4—H4B	109.5	C29—C28—C33	119.7 (7)
C3—C4—H4C	109.5	C29—C28—N4	121.9 (7)
H4A—C4—H4C	109.5	C33—C28—N4	118.3 (7)
H4B—C4—H4C	109.5	C28—C29—C30	121.5 (7)
O5—C5—O6	124.5 (6)	C28—C29—H29	119.3
O5—C5—C6	118.9 (6)	C30—C29—H29	119.3
O6—C5—C6	116.6 (6)	C31—C30—C29	117.4 (8)
C5—C6—H6A	109.5	C31—C30—C34	123.1 (8)
C5—C6—H6B	109.5	C29—C30—C34	119.5 (8)
H6A—C6—H6B	109.5	C30—C31—C32	121.1 (8)
C5—C6—H6C	109.5	C30—C31—H31	119.4
H6A—C6—H6C	109.5	C32—C31—H31	119.4
H6B—C6—H6C	109.5	C33—C32—C31	120.5 (8)
O7—C7—O8	125.5 (6)	C33—C32—H32	119.7
O7—C7—C8	117.3 (6)	C31—C32—H32	119.7
O8—C7—C8	117.1 (7)	C32—C33—C28	119.8 (8)
C7—C8—H8A	109.5	C32—C33—H33	120.1
C7—C8—H8B	109.5	C28—C33—H33	120.1
H8A—C8—H8B	109.5	C30—C34—H34A	109.5
C7—C8—H8C	109.5	C30—C34—H34B	109.5
H8A—C8—H8C	109.5	H34A—C34—H34B	109.5
H8B—C8—H8C	109.5	C30—C34—H34C	109.5
N1—C9—C10	124.9 (6)	H34A—C34—H34C	109.5
N1—C9—H9	117.5	H34B—C34—H34C	109.5

O8—Cu1—Cu2—O5	−86.6 (2)	Cu2—Cu1—O8—C7	−4.0 (5)
O4—Cu1—Cu2—O5	93.9 (2)	Cu2—O2—C1—O1	−0.5 (10)
O6—Cu1—Cu2—O5	4.4 (2)	Cu2—O2—C1—C2	−179.9 (5)
O1—Cu1—Cu2—O5	−177.0 (2)	Cu1—O1—C1—O2	7.4 (10)
O8—Cu1—Cu2—O2	95.1 (2)	Cu1—O1—C1—C2	−173.1 (5)
O4—Cu1—Cu2—O2	−84.3 (2)	Cu1—O4—C3—O3	−0.7 (9)
O6—Cu1—Cu2—O2	−173.9 (2)	Cu1—O4—C3—C4	179.5 (5)
O1—Cu1—Cu2—O2	4.8 (2)	Cu2—O3—C3—O4	5.0 (9)
O8—Cu1—Cu2—O7	3.9 (2)	Cu2—O3—C3—C4	−175.2 (5)
O4—Cu1—Cu2—O7	−175.6 (2)	Cu2—O5—C5—O6	2.5 (9)
O6—Cu1—Cu2—O7	94.8 (2)	Cu2—O5—C5—C6	−178.3 (5)
O1—Cu1—Cu2—O7	−86.5 (2)	Cu1—O6—C5—O5	3.7 (10)
O8—Cu1—Cu2—O3	−177.5 (2)	Cu1—O6—C5—C6	−175.5 (5)
O4—Cu1—Cu2—O3	3.0 (2)	Cu2—O7—C7—O8	4.3 (9)
O6—Cu1—Cu2—O3	−86.6 (2)	Cu2—O7—C7—C8	−176.4 (4)
O1—Cu1—Cu2—O3	92.1 (2)	Cu1—O8—C7—O7	1.2 (9)
O8—Cu1—N1—C9	73.9 (5)	Cu1—O8—C7—C8	−178.1 (4)
O4—Cu1—N1—C9	−106.6 (5)	C13—N1—C9—C10	−1.2 (10)
O6—Cu1—N1—C9	−16.5 (5)	Cu1—N1—C9—C10	−172.9 (6)
O1—Cu1—N1—C9	163.6 (5)	N1—C9—C10—C11	1.0 (12)
O8—Cu1—N1—C13	−96.5 (5)	C9—C10—C11—C12	−0.7 (10)
O4—Cu1—N1—C13	83.0 (5)	C9—C10—C11—C14	177.8 (7)
O6—Cu1—N1—C13	173.1 (5)	C10—C11—C12—C13	0.9 (10)
O1—Cu1—N1—C13	−6.9 (5)	C14—C11—C12—C13	−177.6 (7)
O5—Cu2—N3—C26	−117.0 (6)	C9—N1—C13—N2	−175.8 (6)
O2—Cu2—N3—C26	61.6 (6)	Cu1—N1—C13—N2	−5.6 (8)
O7—Cu2—N3—C26	153.3 (6)	C9—N1—C13—C12	1.3 (9)
O3—Cu2—N3—C26	−26.8 (6)	Cu1—N1—C13—C12	171.5 (4)
O5—Cu2—N3—C22	56.7 (6)	C15—N2—C13—N1	−176.0 (6)
O2—Cu2—N3—C22	−124.7 (6)	C15—N2—C13—C12	6.9 (11)
O7—Cu2—N3—C22	−33.1 (6)	C11—C12—C13—N1	−1.2 (9)
O3—Cu2—N3—C22	146.9 (5)	C11—C12—C13—N2	175.7 (6)
O8—Cu1—O1—C1	−92.0 (6)	C13—N2—C15—C20	−134.6 (7)
O4—Cu1—O1—C1	77.1 (6)	C13—N2—C15—C16	49.4 (10)
O6—Cu1—O1—C1	−2.5 (12)	C20—C15—C16—C17	−0.3 (10)
N1—Cu1—O1—C1	177.4 (5)	N2—C15—C16—C17	175.7 (6)
Cu2—Cu1—O1—C1	−7.7 (5)	C15—C16—C17—C18	−0.6 (10)
O5—Cu2—O2—C1	−13.1 (15)	C15—C16—C17—C21	−178.9 (7)
O7—Cu2—O2—C1	78.8 (5)	C16—C17—C18—C19	0.4 (13)
O3—Cu2—O2—C1	−87.0 (5)	C21—C17—C18—C19	178.7 (9)
N3—Cu2—O2—C1	174.4 (5)	C17—C18—C19—C20	0.8 (14)
Cu1—Cu2—O2—C1	−4.0 (5)	C16—C15—C20—C19	1.5 (11)
O5—Cu2—O3—C3	−88.6 (5)	N2—C15—C20—C19	−174.6 (7)
O2—Cu2—O3—C3	80.8 (5)	C18—C19—C20—C15	−1.7 (13)
O7—Cu2—O3—C3	0.7 (12)	C26—N3—C22—C23	0.6 (12)
N3—Cu2—O3—C3	−179.1 (5)	Cu2—N3—C22—C23	−173.8 (7)
Cu1—Cu2—O3—C3	−5.0 (5)	N3—C22—C23—C24	1.6 (13)
O8—Cu1—O4—C3	−5.3 (15)	C22—C23—C24—C25	−2.7 (12)
O6—Cu1—O4—C3	81.3 (5)	C22—C23—C24—C27	177.3 (8)
O1—Cu1—O4—C3	−84.0 (5)	C23—C24—C25—C26	1.8 (12)
N1—Cu1—O4—C3	177.4 (5)	C27—C24—C25—C26	−178.2 (8)
Cu2—Cu1—O4—C3	−2.4 (5)	C22—N3—C26—N4	−179.6 (7)
O2—Cu2—O5—C5	4.1 (15)	Cu2—N3—C26—N4	−6.0 (10)
O7—Cu2—O5—C5	−87.9 (5)	C22—N3—C26—C25	−1.6 (11)
O3—Cu2—O5—C5	77.7 (5)	Cu2—N3—C26—C25	172.0 (6)
N3—Cu2—O5—C5	176.8 (5)	C28—N4—C26—N3	−171.1 (7)
Cu1—Cu2—O5—C5	−5.0 (5)	C28—N4—C26—C25	10.9 (13)
O8—Cu1—O6—C5	78.6 (5)	C24—C25—C26—N3	0.4 (12)
O4—Cu1—O6—C5	−90.3 (5)	C24—C25—C26—N4	178.3 (8)
O1—Cu1—O6—C5	−10.7 (12)	C26—N4—C28—C29	44.1 (12)
N1—Cu1—O6—C5	169.4 (5)	C26—N4—C28—C33	−139.0 (8)
Cu2—Cu1—O6—C5	−5.6 (5)	C33—C28—C29—C30	−0.4 (11)
O5—Cu2—O7—C7	78.3 (5)	N4—C28—C29—C30	176.4 (7)
O2—Cu2—O7—C7	−90.7 (5)	C28—C29—C30—C31	0.5 (12)
O3—Cu2—O7—C7	−11.1 (12)	C28—C29—C30—C34	−178.3 (8)
N3—Cu2—O7—C7	168.8 (5)	C29—C30—C31—C32	−0.4 (14)
Cu1—Cu2—O7—C7	−5.4 (5)	C34—C30—C31—C32	178.4 (10)
O4—Cu1—O8—C7	−1.1 (15)	C30—C31—C32—C33	0.1 (17)
O6—Cu1—O8—C7	−87.5 (5)	C31—C32—C33—C28	0.1 (16)
O1—Cu1—O8—C7	77.5 (5)	C29—C28—C33—C32	0.0 (13)
N1—Cu1—O8—C7	176.3 (5)	N4—C28—C33—C32	−176.9 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.99	2.830 (6)	165
N4—H4···O3	0.86	2.18	2.964 (8)	152

Experimental details

Crystal data
Chemical formula	[Cu₂(C₂H₃O₂)₄(C₁₃H₁₄N₂)₂]
M_r	759.78
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.2489 (4), 14.2110 (7), 16.4484 (8)
α, β, γ (°)	107.798 (1), 101.971 (1), 97.661 (1)
V (Å³)	1755.45 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.27
Crystal size (mm)	0.40 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.631, 0.884
No. of measured, independent and observed [I > 2σ(I)] reflections	21605, 7963, 6719
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.231, 1.12
No. of reflections	7963
No. of parameters	442
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.01, −0.91

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu1—O1	1.985 (4)	Cu2—O2	1.968 (4)
Cu1—O4	1.961 (5)	Cu2—O3	2.001 (5)
Cu1—O6	1.963 (4)	Cu2—O5	1.957 (5)
Cu1—O8	1.956 (5)	Cu2—O7	1.981 (5)
Cu1—N1	2.215 (5)	Cu2—N3	2.208 (5)
Cu1—Cu2	2.6576 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.99	2.830 (6)	165
N4—H4···O3	0.86	2.18	2.964 (8)	152

Acknowledgements

We thank the University of Malaya (grant No. RG027/09AFR, PS374/09 A) for supporting this study.

References

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