Tetra-μ-acetato-κ8O:O′-bis­{[4-methyl-N-(4-methyl­phen­yl)pyridin-2-amine-κN1]copper(II)}

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

doi:10.1107/S1600536810031168

Tetra-μ-acetato-κ⁸O:O′-bis{[4-methyl-N-(4-methylphenyl)pyridin-2-amine-κN¹]copper(II)}

Z. A. Fairuz, Z. Aiyub, Z. Abdullah, S. W. Ng and E. R. T. Tiekink

The title complex, [Cu₂(CH₃COO)₄(C₁₃H₁₄N₂)₂], features a binuclear molecule, which lies about a crystallographic centre of inversion; the four acetate ions each bridge a pair of Cu^II atoms. The coordination of the metal atom is distorted octahedral within a donor set defined by four O atoms, the heterocyclic N atom and the second Cu atom. The pyridine ring is twisted with respect to the tolyl ring and forms a dihedral angle of 35.34 (9)°. A bifurcated N—H

(O,O) hydrogen bond is present, linking the amine group to two carboxylate O atoms derived from different acetate ions. In the crystal, C—H

π interactions link molecules into a supramolecular array in the bc plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810031168/hb5591sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810031168/hb5591Isup2.hkl Contains datablock I

CCDC reference: 792256

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.027
wR factor = 0.083
Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C10
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          5
            CU1 -CU1 -N1  -C5    142.00  3.00   3.666   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         10
            CU1 -CU1 -N1  -C9    -38.00  3.00   3.666   1.555   1.555   1.555
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.11 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   7 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In connection with on-going studies into the structural characterization of tetrakisacetatobis[(substituted 2-aminopyridyl)copper] complexes, see: Barquín et al., 2004; Seco et al., 2004; Sieroń, 2004; Fairuz et al., 2010), the binuclear title complex, (I), was investigated.

The binuclear copper(II) complex, Fig. 1, is situated about a centre of inversion and features two Cu^II atoms bridged by four acetate groups. The Cu–O bond distances lie in a narrow range, i.e. 1.9701 (13) to 1.9759 (13) Å, Table 1. The distorted octahedral coordination environment for the Cu atom is completed by a pyridine-N atom derived from the 4-methyl-N-p-tolylpyridin-2-amine ligand and the second Cu atom [Cu···Cuⁱ = 2.6480 (4) Å for i: 1 - x, 1 - y, 1 - z]. Two intramolecular N1–H···O interactions are noted in which the amine-H spans carboxylate-O atoms derived from different ligands, Table 2. The dihedral angle formed between the pyridine and benzene rings of 35.34 (9) ° indicates the N-heterocycle is non-planar. The major twist in the molecule occurs around the amine group as seen in the value of the C9–N2–C11–C12 torsion angle of -27.2 (3) °. In the crystal packing, contacts of the type C–H···π occur between methyl-H and pyridine rings, Table 2, and lead to the formation of supramolecular arrays in the bc plane, Fig. 2. Layers thus formed stack along the a axis, Fig. 3.

Related literature top

For examples of tetrakisacetatobis[(substituted 2-aminopyridyl)copper] complexes, see: Barquín et al. (2004); Seco et al. (2004); Sieroń (2004); Fairuz et al. (2010).

Experimental top

Copper acetate (0.1 g, 0.5 mmol) dissolved in acetonitrile (15 ml) was added to a mixture of 4-methyl-N-p-tolylpyridin-2-amine (0.2183 g, 1.1 mmol) and trimethyl orthoformate (10 ml). The mixture was heated at 323 K, the green precipitate was collected and recrystallization from its acetonitrile solution yielded green prisms of (I).

Structure description top

For examples of tetrakisacetatobis[(substituted 2-aminopyridyl)copper] complexes, see: Barquín et al. (2004); Seco et al. (2004); Sieroń (2004); Fairuz et al. (2010).

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 displacement ellipsoids at the 50% probability level. Symmetry code: (i) 1 - x, 1 - y, 1 - z.
	Fig. 2. Supramolecular arrays in the bc plane in (I) mediated by C–H···π interactions shown as purple dashed lines.
	Fig. 3. Unit-cell contents shown in projection down the c axis in (I) showing the stacking of layers along a. The C–H···π contacts are shown as purple dashed lines.

Tetra-µ-acetato-κ⁸O:O'-bis{[4-methyl-N-(4- methylphenyl)pyridin-2-amine-κN¹]copper(II)} top

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₁₃H₁₄N₂)₂]	F(000) = 788
M_r = 759.78	D_x = 1.486 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8249 reflections
a = 11.7519 (6) Å	θ = 4.3–28.2°
b = 15.5822 (8) Å	µ = 1.31 mm⁻¹
c = 9.9050 (5) Å	T = 293 K
β = 110.5698 (6)°	Prism, green
V = 1698.17 (15) Å³	0.40 × 0.20 × 0.10 mm
Z = 2

Data collection top

Bruker SMART APEX CCD diffractometer	3890 independent reflections
Radiation source: fine-focus sealed tube	3462 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scan	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→15
T_min = 0.648, T_max = 0.746	k = −20→19
16009 measured reflections	l = −12→12

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0493P)² + 0.7683P] where P = (F_o² + 2F_c²)/3
3890 reflections	(Δ/σ)_max = 0.001
225 parameters	Δρ_max = 0.32 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Cu₂(C₂H₃O₂)₄(C₁₃H₁₄N₂)₂]	V = 1698.17 (15) Å³
M_r = 759.78	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7519 (6) Å	µ = 1.31 mm⁻¹
b = 15.5822 (8) Å	T = 293 K
c = 9.9050 (5) Å	0.40 × 0.20 × 0.10 mm
β = 110.5698 (6)°

Data collection top

Bruker SMART APEX CCD diffractometer	3890 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3462 reflections with I > 2σ(I)
T_min = 0.648, T_max = 0.746	R_int = 0.019
16009 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	1 restraint
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.32 e Å⁻³
3890 reflections	Δρ_min = −0.26 e Å⁻³
225 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.

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.

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

	x	y	z	U_iso*/U_eq
Cu1	0.566326 (17)	0.523188 (13)	0.42225 (2)	0.02759 (8)
N1	0.67899 (13)	0.56104 (9)	0.29545 (15)	0.0288 (3)
N2	0.83831 (15)	0.60834 (13)	0.48943 (17)	0.0431 (4)
H2n	0.7883 (19)	0.6036 (17)	0.533 (3)	0.060 (8)*
O1	0.59163 (14)	0.62952 (9)	0.53779 (16)	0.0456 (3)
O2	0.47897 (13)	0.59061 (9)	0.66720 (15)	0.0416 (3)
O3	0.41276 (12)	0.56868 (10)	0.28515 (15)	0.0449 (3)
O4	0.30200 (12)	0.52953 (10)	0.41638 (16)	0.0444 (3)
C1	0.54512 (15)	0.64284 (11)	0.63233 (19)	0.0319 (4)
C2	0.5712 (2)	0.72788 (14)	0.7088 (3)	0.0476 (5)
H2A	0.6411	0.7535	0.6962	0.071*
H2B	0.5870	0.7194	0.8098	0.071*
H2C	0.5023	0.7651	0.6694	0.071*
C3	0.31446 (16)	0.56196 (12)	0.30683 (19)	0.0343 (4)
C4	0.2011 (2)	0.59515 (18)	0.1922 (3)	0.0570 (6)
H4A	0.1309	0.5714	0.2067	0.086*
H4B	0.2013	0.5786	0.0989	0.086*
H4C	0.1989	0.6566	0.1979	0.086*
C5	0.62691 (17)	0.54835 (13)	0.1533 (2)	0.0376 (4)
H5	0.5491	0.5250	0.1193	0.045*
C6	0.68042 (18)	0.56738 (15)	0.0545 (2)	0.0426 (5)
H6	0.6405	0.5564	−0.0431	0.051*
C7	0.79636 (18)	0.60370 (13)	0.1037 (2)	0.0381 (4)
C8	0.85144 (16)	0.61737 (12)	0.24918 (19)	0.0342 (4)
H8	0.9286	0.6417	0.2848	0.041*
C9	0.79178 (15)	0.59485 (11)	0.34396 (18)	0.0287 (3)
C10	0.8574 (2)	0.6289 (2)	−0.0006 (2)	0.0594 (7)
H10A	0.9330	0.5986	0.0225	0.089*
H10B	0.8725	0.6895	0.0059	0.089*
H10C	0.8056	0.6146	−0.0969	0.089*
C11	0.95658 (16)	0.62975 (12)	0.58042 (17)	0.0313 (4)
C12	1.06199 (17)	0.60942 (12)	0.5541 (2)	0.0351 (4)
H12	1.0573	0.5808	0.4700	0.042*
C13	1.17443 (17)	0.63203 (13)	0.6539 (2)	0.0383 (4)
H13	1.2441	0.6197	0.6335	0.046*
C14	1.18612 (17)	0.67236 (13)	0.7825 (2)	0.0391 (4)
C15	1.07993 (18)	0.69041 (14)	0.8091 (2)	0.0422 (4)
H15	1.0848	0.7165	0.8954	0.051*
C16	0.96734 (17)	0.67014 (14)	0.7092 (2)	0.0382 (4)
H16	0.8976	0.6838	0.7286	0.046*
C17	1.3088 (2)	0.69482 (19)	0.8908 (3)	0.0605 (6)
H17A	1.3591	0.7183	0.8416	0.091*
H17B	1.3464	0.6441	0.9423	0.091*
H17C	1.2993	0.7364	0.9575	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02400 (12)	0.03200 (13)	0.02806 (12)	−0.00382 (8)	0.01077 (8)	−0.00001 (7)
N1	0.0256 (7)	0.0335 (7)	0.0283 (7)	−0.0050 (6)	0.0107 (5)	−0.0009 (6)
N2	0.0290 (8)	0.0746 (12)	0.0281 (7)	−0.0196 (8)	0.0129 (6)	−0.0065 (7)
O1	0.0547 (9)	0.0384 (7)	0.0547 (8)	−0.0154 (6)	0.0331 (7)	−0.0131 (6)
O2	0.0451 (8)	0.0390 (7)	0.0475 (8)	−0.0118 (6)	0.0248 (6)	−0.0106 (6)
O3	0.0342 (7)	0.0612 (9)	0.0396 (7)	0.0082 (7)	0.0133 (6)	0.0156 (7)
O4	0.0285 (7)	0.0626 (10)	0.0407 (7)	0.0018 (6)	0.0102 (6)	0.0122 (6)
C1	0.0273 (8)	0.0305 (8)	0.0353 (9)	−0.0009 (7)	0.0076 (7)	−0.0028 (7)
C2	0.0500 (12)	0.0361 (10)	0.0557 (12)	−0.0078 (9)	0.0172 (10)	−0.0128 (9)
C3	0.0299 (9)	0.0369 (9)	0.0320 (8)	0.0046 (7)	0.0057 (7)	0.0001 (7)
C4	0.0399 (11)	0.0736 (16)	0.0467 (12)	0.0173 (11)	0.0017 (9)	0.0116 (11)
C5	0.0312 (9)	0.0492 (10)	0.0314 (9)	−0.0133 (8)	0.0097 (7)	−0.0049 (8)
C6	0.0404 (10)	0.0600 (13)	0.0270 (8)	−0.0120 (9)	0.0114 (7)	−0.0047 (8)
C7	0.0368 (9)	0.0497 (11)	0.0326 (9)	−0.0042 (8)	0.0183 (8)	0.0027 (8)
C8	0.0265 (8)	0.0438 (10)	0.0334 (8)	−0.0072 (7)	0.0120 (7)	0.0038 (7)
C9	0.0261 (8)	0.0316 (8)	0.0291 (8)	−0.0032 (6)	0.0107 (6)	−0.0002 (6)
C10	0.0529 (13)	0.0952 (19)	0.0381 (11)	−0.0155 (13)	0.0260 (10)	0.0041 (12)
C11	0.0277 (8)	0.0370 (9)	0.0283 (8)	−0.0073 (7)	0.0086 (6)	0.0016 (6)
C12	0.0355 (9)	0.0372 (9)	0.0335 (9)	−0.0017 (7)	0.0133 (7)	−0.0034 (7)
C13	0.0276 (8)	0.0427 (10)	0.0445 (10)	0.0012 (8)	0.0125 (8)	0.0025 (8)
C14	0.0301 (9)	0.0421 (10)	0.0386 (9)	−0.0039 (8)	0.0041 (7)	0.0025 (8)
C15	0.0406 (10)	0.0513 (11)	0.0316 (9)	−0.0028 (9)	0.0090 (8)	−0.0080 (8)
C16	0.0299 (9)	0.0535 (11)	0.0333 (9)	−0.0021 (8)	0.0135 (7)	−0.0029 (8)
C17	0.0357 (11)	0.0785 (17)	0.0535 (13)	−0.0105 (11)	−0.0015 (10)	−0.0050 (12)

Geometric parameters (Å, º) top

Cu1—O2ⁱ	1.9701 (13)	C5—C6	1.368 (3)
Cu1—O3	1.9702 (14)	C5—H5	0.9300
Cu1—O4ⁱ	1.9713 (14)	C6—C7	1.396 (3)
Cu1—O1	1.9759 (13)	C6—H6	0.9300
Cu1—N1	2.2016 (14)	C7—C8	1.373 (3)
Cu1—Cu1ⁱ	2.6480 (4)	C7—C10	1.502 (3)
N1—C5	1.339 (2)	C8—C9	1.400 (2)
N1—C9	1.348 (2)	C8—H8	0.9300
N2—C9	1.366 (2)	C10—H10A	0.9600
N2—C11	1.405 (2)	C10—H10B	0.9600
N2—H2n	0.85 (3)	C10—H10C	0.9600
O1—C1	1.256 (2)	C11—C16	1.388 (2)
O2—C1	1.255 (2)	C11—C12	1.389 (3)
O2—Cu1ⁱ	1.9701 (13)	C12—C13	1.389 (3)
O3—C3	1.251 (2)	C12—H12	0.9300
O4—C3	1.251 (2)	C13—C14	1.384 (3)
O4—Cu1ⁱ	1.9713 (14)	C13—H13	0.9300
C1—C2	1.504 (3)	C14—C15	1.391 (3)
C2—H2A	0.9600	C14—C17	1.505 (3)
C2—H2B	0.9600	C15—C16	1.382 (3)
C2—H2C	0.9600	C15—H15	0.9300
C3—C4	1.506 (3)	C16—H16	0.9300
C4—H4A	0.9600	C17—H17A	0.9600
C4—H4B	0.9600	C17—H17B	0.9600
C4—H4C	0.9600	C17—H17C	0.9600

O2ⁱ—Cu1—O3	88.66 (7)	N1—C5—H5	117.8
O2ⁱ—Cu1—O4ⁱ	90.04 (7)	C6—C5—H5	117.8
O3—Cu1—O4ⁱ	167.64 (6)	C5—C6—C7	118.40 (17)
O2ⁱ—Cu1—O1	167.72 (6)	C5—C6—H6	120.8
O3—Cu1—O1	90.72 (7)	C7—C6—H6	120.8
O4ⁱ—Cu1—O1	87.95 (7)	C8—C7—C6	118.17 (16)
O2ⁱ—Cu1—N1	96.10 (5)	C8—C7—C10	121.22 (18)
O3—Cu1—N1	95.70 (5)	C6—C7—C10	120.60 (18)
O4ⁱ—Cu1—N1	96.67 (6)	C7—C8—C9	120.16 (16)
O1—Cu1—N1	96.17 (5)	C7—C8—H8	119.9
O2ⁱ—Cu1—Cu1ⁱ	83.96 (4)	C9—C8—H8	119.9
O3—Cu1—Cu1ⁱ	85.14 (4)	N1—C9—N2	114.53 (14)
O4ⁱ—Cu1—Cu1ⁱ	82.50 (4)	N1—C9—C8	121.36 (15)
O1—Cu1—Cu1ⁱ	83.77 (4)	N2—C9—C8	124.04 (16)
N1—Cu1—Cu1ⁱ	179.17 (4)	C7—C10—H10A	109.5
C5—N1—C9	117.49 (14)	C7—C10—H10B	109.5
C5—N1—Cu1	114.60 (11)	H10A—C10—H10B	109.5
C9—N1—Cu1	127.91 (11)	C7—C10—H10C	109.5
C9—N2—C11	130.71 (15)	H10A—C10—H10C	109.5
C9—N2—H2n	115.7 (18)	H10B—C10—H10C	109.5
C11—N2—H2n	113.6 (18)	C16—C11—C12	118.46 (16)
C1—O1—Cu1	123.64 (12)	C16—C11—N2	116.57 (16)
C1—O2—Cu1ⁱ	123.75 (12)	C12—C11—N2	124.87 (16)
C3—O3—Cu1	121.93 (12)	C13—C12—C11	119.80 (17)
C3—O4—Cu1ⁱ	125.01 (12)	C13—C12—H12	120.1
O1—C1—O2	124.88 (16)	C11—C12—H12	120.1
O1—C1—C2	117.13 (17)	C12—C13—C14	122.15 (18)
O2—C1—C2	117.99 (17)	C12—C13—H13	118.9
C1—C2—H2A	109.5	C14—C13—H13	118.9
C1—C2—H2B	109.5	C13—C14—C15	117.41 (17)
H2A—C2—H2B	109.5	C13—C14—C17	121.47 (19)
C1—C2—H2C	109.5	C15—C14—C17	121.1 (2)
H2A—C2—H2C	109.5	C16—C15—C14	121.02 (18)
H2B—C2—H2C	109.5	C16—C15—H15	119.5
O4—C3—O3	125.38 (17)	C14—C15—H15	119.5
O4—C3—C4	116.79 (18)	C15—C16—C11	121.12 (18)
O3—C3—C4	117.83 (18)	C15—C16—H16	119.4
C3—C4—H4A	109.5	C11—C16—H16	119.4
C3—C4—H4B	109.5	C14—C17—H17A	109.5
H4A—C4—H4B	109.5	C14—C17—H17B	109.5
C3—C4—H4C	109.5	H17A—C17—H17B	109.5
H4A—C4—H4C	109.5	C14—C17—H17C	109.5
H4B—C4—H4C	109.5	H17A—C17—H17C	109.5
N1—C5—C6	124.41 (17)	H17B—C17—H17C	109.5

O2ⁱ—Cu1—N1—C5	48.27 (14)	C9—N1—C5—C6	0.0 (3)
O3—Cu1—N1—C5	−40.99 (15)	Cu1—N1—C5—C6	179.90 (18)
O4ⁱ—Cu1—N1—C5	139.02 (14)	N1—C5—C6—C7	−1.0 (3)
O1—Cu1—N1—C5	−132.33 (14)	C5—C6—C7—C8	0.9 (3)
Cu1ⁱ—Cu1—N1—C5	142 (3)	C5—C6—C7—C10	−177.7 (2)
O2ⁱ—Cu1—N1—C9	−131.83 (15)	C6—C7—C8—C9	0.2 (3)
O3—Cu1—N1—C9	138.92 (15)	C10—C7—C8—C9	178.8 (2)
O4ⁱ—Cu1—N1—C9	−41.07 (15)	C5—N1—C9—N2	178.27 (18)
O1—Cu1—N1—C9	47.58 (15)	Cu1—N1—C9—N2	−1.6 (2)
Cu1ⁱ—Cu1—N1—C9	−38 (3)	C5—N1—C9—C8	1.2 (3)
O2ⁱ—Cu1—O1—C1	−2.9 (4)	Cu1—N1—C9—C8	−178.74 (13)
O3—Cu1—O1—C1	84.09 (16)	C11—N2—C9—N1	169.2 (2)
O4ⁱ—Cu1—O1—C1	−83.62 (16)	C11—N2—C9—C8	−13.8 (3)
N1—Cu1—O1—C1	179.90 (16)	C7—C8—C9—N1	−1.3 (3)
Cu1ⁱ—Cu1—O1—C1	−0.94 (15)	C7—C8—C9—N2	−178.1 (2)
O2ⁱ—Cu1—O3—C3	82.85 (16)	C9—N2—C11—C16	156.4 (2)
O4ⁱ—Cu1—O3—C3	−1.2 (4)	C9—N2—C11—C12	−27.2 (3)
O1—Cu1—O3—C3	−84.89 (16)	C16—C11—C12—C13	−2.0 (3)
N1—Cu1—O3—C3	178.84 (16)	N2—C11—C12—C13	−178.34 (18)
Cu1ⁱ—Cu1—O3—C3	−1.20 (15)	C11—C12—C13—C14	2.0 (3)
Cu1—O1—C1—O2	1.2 (3)	C12—C13—C14—C15	−0.4 (3)
Cu1—O1—C1—C2	−178.81 (14)	C12—C13—C14—C17	178.7 (2)
Cu1ⁱ—O2—C1—O1	−0.6 (3)	C13—C14—C15—C16	−1.2 (3)
Cu1ⁱ—O2—C1—C2	179.40 (14)	C17—C14—C15—C16	179.7 (2)
Cu1ⁱ—O4—C3—O3	−2.7 (3)	C14—C15—C16—C11	1.2 (3)
Cu1ⁱ—O4—C3—C4	177.10 (15)	C12—C11—C16—C15	0.4 (3)
Cu1—O3—C3—O4	2.6 (3)	N2—C11—C16—C15	177.08 (19)
Cu1—O3—C3—C4	−177.18 (15)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1,C5–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O1	0.85 (3)	2.36 (2)	3.117 (3)	149 (2)
N2—H2n···O4ⁱ	0.85 (3)	2.46 (3)	3.047 (2)	127 (2)
C2—H2a···Cg1ⁱⁱ	0.96	2.80	3.566 (2)	138

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₂H₃O₂)₄(C₁₃H₁₄N₂)₂]
M_r	759.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.7519 (6), 15.5822 (8), 9.9050 (5)
β (°)	110.5698 (6)
V (Å³)	1698.17 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.31
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.648, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	16009, 3890, 3462
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.083, 1.01
No. of reflections	3890
No. of parameters	225
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.26

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—O2ⁱ	1.9701 (13)	Cu1—O1	1.9759 (13)
Cu1—O3	1.9702 (14)	Cu1—N1	2.2016 (14)
Cu1—O4ⁱ	1.9713 (14)	Cu1—Cu1ⁱ	2.6480 (4)