Tetra-μ-methacrylato-κ8O:O′-bis­[(pyri­din-2-amine-κN1)copper(II)]

Zhang, X.-Y.

doi:10.1107/S160053680901352X

Tetra-μ-methacrylato-κ⁸O:O′-bis[(pyridin-2-amine-κN¹)copper(II)]

In the title carboxylate-bridged binuclear copper complex, [Cu₂(C₄H₅O₂)₄(C₅H₆N₂)₂], each Cu^II ion has a distorted square-based pyramidal environment formed by one N and four O atoms. The asymmetric unit contains two halves of two centrosymmetric molecules, with Cu

Cu separations of 2.6498 (8) and 2.6528 (8) Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680901352X/cv2539sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680901352X/cv2539Isup2.hkl Contains datablock I

CCDC reference: 731152

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R factor = 0.041
wR factor = 0.084
Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   298.000
            Value of melting point given =     0.000
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.69 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     --  C19     ..       5.78 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C7     --  C9      ..       6.14 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT362_ALERT_2_C Short  C(sp3)-C(sp2) Bond  C11    -   C13    ...       1.41 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4B    ...          ?

Alert level G
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.14 Ratio

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

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

Comment top

In continuation of structural study of paddle-wheel copper(II) carboxylate compounds (Wu & Wang, 2004; Du et al., 2002), we report here the crystal structure of the title complex, (I).

The title compound (Figure 1) contains two independent dinuclear cage Cu^II complexes, each with inversion symmetry. In each dimer, two Cu^II atoms are connected by four carboxylate groups from methacrylate ends, forming a cage structure, and the N atoms from the pyridin-2-amine ligands are binded to Cu^II centers in the terminal positions, which is very similar the [Cu₂{CH₂C(CH₃)COO}₄(C₅H₅N)₂] compound (Wu & Wang, 2004). In the title compound, the amino groups are involved in hydrogen-bonded interactions with carboxylate groups (Table 1). The Cu···Cu separations of 2.6498 (8) and 2.6528 (8) Å are a little longer than those in [Cu₂{CH₂C(CH₃)COO}₄(C₅H₅N)₂] (Wu & Wang, 2004), that may be attributed to the steric effect from amino group in the assembling process.

Related literature top

For the crystal structures of related binuclear complexes, see: Du et al. (2002); Wu et al. (2004).

Experimental top

Pyridin-2-amine (0.042 g, 0.28 mmol), [Cu₂{CH₂C(CH₃)COO}₄.2H₂O] (0.025 g, 0.13 mmol), were added distilled methanol(20 mL), the mixture was heated for ten hours under reflux. during the process stirring and influx were required. The resultant was kept at room temperature, two days later single crystals suitable for X-ray diffraction measurement were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A portion of the title cystal structure showing two independent dinuclear complexes with the atom-labeling scheme [symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+1, -y, -z+1]. Displacement ellipsoids are shown at the 30% probability level.

Tetra-µ-methacrylato-κ⁸O:O'-bis[(pyridin-2-amine- κN¹)copper(II)] top

Crystal data top

[Cu₂(C₄H₅O₂)₄(C₅H₆N₂)₂]	F(000) = 1352
M_r = 655.64	D_x = 1.447 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5539 reflections
a = 16.8591 (15) Å	θ = 2.2–25.4°
b = 12.1185 (11) Å	µ = 1.47 mm⁻¹
c = 16.5980 (15) Å	T = 298 K
β = 117.458 (2)°	Block, blue
V = 3009.1 (5) Å³	0.28 × 0.20 × 0.13 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	5539 independent reflections
Radiation source: fine-focus sealed tube	3542 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
ϕ and ω scans	θ_max = 25.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −20→20
T_min = 0.685, T_max = 0.832	k = −14→10
15356 measured reflections	l = −20→20

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 0.88	w = 1/[σ²(F_o²) + (0.01P)² + 0.272P] where P = (F_o² + 2F_c²)/3
5539 reflections	(Δ/σ)_max = 0.001
365 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Cu₂(C₄H₅O₂)₄(C₅H₆N₂)₂]	V = 3009.1 (5) Å³
M_r = 655.64	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.8591 (15) Å	µ = 1.47 mm⁻¹
b = 12.1185 (11) Å	T = 298 K
c = 16.5980 (15) Å	0.28 × 0.20 × 0.13 mm
β = 117.458 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	5539 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3542 reflections with I > 2σ(I)
T_min = 0.685, T_max = 0.832	R_int = 0.099
15356 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 0.88	Δρ_max = 0.50 e Å⁻³
5539 reflections	Δρ_min = −0.35 e Å⁻³
365 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Cu2	0.45444 (2)	0.09186 (3)	0.49285 (2)	0.04205 (13)
O6	0.57214 (14)	0.1643 (2)	0.55362 (14)	0.0594 (7)
O5	0.64848 (13)	0.0105 (2)	0.56541 (14)	0.0568 (6)
O7	0.46883 (14)	0.0508 (2)	0.61306 (13)	0.0559 (6)
O8	0.45651 (13)	0.1057 (2)	0.37567 (13)	0.0531 (6)
N1	0.37557 (15)	0.2416 (2)	0.47289 (15)	0.0420 (7)
N2	0.26243 (18)	0.1607 (3)	0.4918 (2)	0.0837 (11)
H2A	0.2881	0.0979	0.4969	0.100*
H2B	0.2133	0.1647	0.4955	0.100*
C1	0.4104 (2)	0.3339 (3)	0.45853 (19)	0.0498 (9)
H1	0.4633	0.3273	0.4542	0.060*
C2	0.3754 (2)	0.4363 (3)	0.4498 (2)	0.0637 (10)
H2	0.4029	0.4976	0.4397	0.076*
C3	0.2970 (3)	0.4456 (4)	0.4565 (2)	0.0739 (12)
H3	0.2711	0.5146	0.4520	0.089*
C4	0.2579 (2)	0.3550 (4)	0.4694 (2)	0.0671 (11)
H4	0.2043	0.3606	0.4725	0.081*
C5	0.2991 (2)	0.2524 (3)	0.4781 (2)	0.0511 (9)
C6	0.6433 (2)	0.1113 (3)	0.5791 (2)	0.0491 (9)
C7	0.7293 (2)	0.1718 (4)	0.6338 (2)	0.0638 (11)
C8	0.7244 (3)	0.2751 (4)	0.6645 (3)	0.123 (2)
H5	0.7764	0.3150	0.6986	0.148*
H6	0.6691	0.3054	0.6514	0.148*
C9	0.8112 (2)	0.1162 (4)	0.6499 (3)	0.0890 (14)
H7	0.8151	0.0472	0.6799	0.134*
H8	0.8614	0.1616	0.6875	0.134*
H9	0.8114	0.1029	0.5930	0.134*
C10	0.5107 (2)	−0.0342 (3)	0.6544 (2)	0.0459 (9)
C11	0.5223 (2)	−0.0509 (4)	0.7493 (2)	0.0596 (10)
C12	0.5509 (2)	−0.1495 (4)	0.7904 (2)	0.0842 (13)
H12A	0.5571	−0.1610	0.8484	0.101*
H12B	0.5645	−0.2058	0.7607	0.101*
C13	0.5006 (3)	0.0384 (5)	0.7901 (3)	0.1203 (19)
H13A	0.5050	0.0153	0.8474	0.180*
H13B	0.4407	0.0623	0.7511	0.180*
H13C	0.5413	0.0982	0.7997	0.180*
Cu1	0.95058 (2)	0.58684 (3)	0.95769 (2)	0.04257 (13)
O2	0.95450 (14)	0.6179 (2)	1.07602 (13)	0.0538 (6)
O1	1.03977 (14)	0.4737 (2)	1.14736 (13)	0.0557 (6)
O4	0.84923 (13)	0.4861 (2)	0.92871 (14)	0.0580 (6)
O3	1.06707 (14)	0.6594 (2)	1.00035 (15)	0.0581 (6)
N3	0.87554 (16)	0.7370 (2)	0.89766 (16)	0.0459 (7)
N4	0.7646 (2)	0.6533 (3)	0.7748 (2)	0.1019 (13)
H4A	0.7880	0.5907	0.7981	0.122*
H4B	0.7171	0.6557	0.7233	0.122*
C14	0.8020 (2)	0.7465 (4)	0.8181 (2)	0.0595 (10)
C15	0.7644 (3)	0.8481 (4)	0.7818 (3)	0.0766 (13)
H14	0.7130	0.8525	0.7264	0.092*
C16	0.8035 (3)	0.9387 (4)	0.8278 (3)	0.0878 (14)
H15	0.7798	1.0075	0.8040	0.105*
C17	0.8792 (3)	0.9320 (4)	0.9108 (3)	0.0791 (12)
H16	0.9065	0.9950	0.9440	0.095*
C18	0.9116 (2)	0.8313 (3)	0.9417 (2)	0.0580 (10)
H18	0.9626	0.8264	0.9974	0.070*
C19	0.9986 (2)	0.5606 (3)	1.1453 (2)	0.0438 (8)
C20	1.0036 (2)	0.6006 (3)	1.2327 (2)	0.0485 (9)
C21	0.9650 (2)	0.7007 (4)	1.2336 (2)	0.0756 (12)
H21A	0.9676	0.7271	1.2874	0.091*
H21B	0.9364	0.7417	1.1805	0.091*
C22	1.0486 (2)	0.5319 (4)	1.3096 (2)	0.0833 (13)
H22A	1.0584	0.5718	1.3634	0.125*
H22B	1.1051	0.5096	1.3139	0.125*
H22C	1.0129	0.4678	1.3037	0.125*
C23	0.8592 (2)	0.3867 (3)	0.9520 (2)	0.0484 (9)
C24	0.7760 (2)	0.3184 (3)	0.9224 (2)	0.0632 (10)
C25	0.6949 (3)	0.3669 (4)	0.8807 (3)	0.1101 (17)
H25A	0.6434	0.3249	0.8636	0.132*
H25B	0.6904	0.4423	0.8691	0.132*
C26	0.7873 (3)	0.2029 (4)	0.9421 (4)	0.1107 (17)
H26A	0.7305	0.1706	0.9287	0.166*
H26B	0.8280	0.1923	1.0052	0.166*
H26C	0.8108	0.1683	0.9057	0.166*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu2	0.0353 (2)	0.0501 (3)	0.0383 (2)	0.00534 (19)	0.01493 (17)	0.0075 (2)
O6	0.0419 (13)	0.0637 (18)	0.0629 (14)	−0.0030 (13)	0.0160 (12)	0.0034 (14)
O5	0.0347 (13)	0.0625 (18)	0.0670 (15)	0.0007 (13)	0.0182 (11)	0.0027 (14)
O7	0.0655 (15)	0.0628 (17)	0.0452 (13)	0.0154 (14)	0.0304 (12)	0.0141 (12)
O8	0.0555 (14)	0.0648 (17)	0.0423 (12)	0.0132 (13)	0.0253 (11)	0.0124 (12)
N1	0.0351 (14)	0.0552 (19)	0.0365 (13)	0.0051 (14)	0.0171 (12)	0.0022 (13)
N2	0.064 (2)	0.088 (3)	0.126 (3)	0.013 (2)	0.067 (2)	0.023 (2)
C1	0.0408 (19)	0.061 (3)	0.0449 (19)	0.0041 (19)	0.0176 (16)	−0.0011 (19)
C2	0.067 (3)	0.050 (3)	0.068 (2)	0.003 (2)	0.027 (2)	0.000 (2)
C3	0.070 (3)	0.066 (3)	0.075 (3)	0.023 (2)	0.025 (2)	−0.007 (2)
C4	0.056 (2)	0.083 (3)	0.069 (3)	0.015 (2)	0.035 (2)	−0.005 (2)
C5	0.047 (2)	0.066 (3)	0.0431 (18)	0.007 (2)	0.0234 (16)	−0.0004 (19)
C6	0.041 (2)	0.064 (3)	0.0389 (19)	−0.007 (2)	0.0156 (17)	0.0116 (19)
C7	0.046 (2)	0.070 (3)	0.063 (2)	−0.010 (2)	0.0150 (19)	0.016 (2)
C8	0.078 (3)	0.084 (4)	0.159 (5)	−0.031 (3)	0.013 (3)	−0.038 (4)
C9	0.054 (2)	0.119 (4)	0.080 (3)	−0.017 (3)	0.019 (2)	0.014 (3)
C10	0.0346 (19)	0.061 (3)	0.0382 (18)	−0.0059 (18)	0.0136 (15)	0.0036 (18)
C11	0.060 (2)	0.081 (3)	0.0368 (19)	0.004 (2)	0.0221 (17)	0.007 (2)
C12	0.104 (3)	0.099 (4)	0.051 (2)	0.012 (3)	0.037 (2)	0.023 (2)
C13	0.181 (5)	0.128 (5)	0.063 (3)	0.028 (4)	0.066 (3)	0.001 (3)
Cu1	0.0397 (2)	0.0478 (3)	0.0397 (2)	0.0095 (2)	0.01785 (18)	0.00255 (19)
O2	0.0624 (14)	0.0598 (16)	0.0409 (12)	0.0190 (13)	0.0254 (11)	0.0052 (12)
O1	0.0651 (15)	0.0638 (18)	0.0424 (12)	0.0192 (14)	0.0283 (11)	0.0022 (12)
O4	0.0377 (13)	0.0662 (18)	0.0614 (14)	0.0051 (13)	0.0154 (11)	0.0078 (14)
O3	0.0415 (13)	0.0556 (17)	0.0765 (15)	0.0017 (12)	0.0267 (12)	0.0023 (14)
N3	0.0377 (15)	0.056 (2)	0.0390 (14)	0.0134 (15)	0.0136 (12)	0.0087 (14)
N4	0.090 (3)	0.105 (3)	0.057 (2)	0.010 (2)	−0.0116 (18)	0.002 (2)
C14	0.052 (2)	0.074 (3)	0.050 (2)	0.014 (2)	0.0207 (19)	0.010 (2)
C15	0.065 (3)	0.099 (4)	0.057 (2)	0.036 (3)	0.020 (2)	0.030 (3)
C16	0.098 (4)	0.079 (4)	0.091 (3)	0.042 (3)	0.047 (3)	0.036 (3)
C17	0.092 (3)	0.059 (3)	0.097 (3)	0.021 (3)	0.054 (3)	0.015 (3)
C18	0.060 (2)	0.054 (3)	0.062 (2)	0.012 (2)	0.0304 (19)	0.006 (2)
C19	0.0379 (18)	0.056 (2)	0.0425 (19)	−0.0068 (18)	0.0229 (16)	−0.0076 (18)
C20	0.0406 (19)	0.066 (3)	0.0394 (18)	−0.0094 (18)	0.0186 (15)	−0.0132 (18)
C21	0.092 (3)	0.084 (3)	0.056 (2)	0.011 (3)	0.038 (2)	−0.019 (2)
C22	0.091 (3)	0.106 (4)	0.052 (2)	0.001 (3)	0.032 (2)	−0.008 (3)
C23	0.047 (2)	0.054 (3)	0.047 (2)	−0.0013 (19)	0.0234 (17)	−0.0084 (18)
C24	0.052 (2)	0.065 (3)	0.071 (2)	−0.005 (2)	0.026 (2)	−0.015 (2)
C25	0.046 (2)	0.087 (4)	0.167 (5)	−0.001 (3)	0.023 (3)	−0.002 (4)
C26	0.083 (3)	0.067 (3)	0.174 (5)	−0.014 (3)	0.052 (3)	−0.008 (4)

Geometric parameters (Å, º) top

Cu2—O7	1.960 (2)	Cu1—O3	1.962 (2)
Cu2—O8	1.968 (2)	Cu1—O1ⁱⁱ	1.966 (2)
Cu2—O6	1.970 (2)	Cu1—O4	1.971 (2)
Cu2—O5ⁱ	1.985 (2)	Cu1—O2	1.971 (2)
Cu2—N1	2.183 (3)	Cu1—N3	2.178 (3)
Cu2—Cu2ⁱ	2.6528 (8)	Cu1—Cu1ⁱⁱ	2.6498 (8)
O6—C6	1.250 (4)	O2—C19	1.253 (4)
O5—C6	1.252 (4)	O1—C19	1.253 (4)
O5—Cu2ⁱ	1.985 (2)	O1—Cu1ⁱⁱ	1.966 (2)
O7—C10	1.258 (4)	O4—C23	1.252 (4)
O8—C10ⁱ	1.249 (4)	O3—C23ⁱⁱ	1.256 (4)
N1—C1	1.335 (4)	N3—C14	1.336 (4)
N1—C5	1.338 (4)	N3—C18	1.341 (4)
N2—C5	1.340 (4)	N4—C14	1.332 (5)
N2—H2A	0.8600	N4—H4A	0.8600
N2—H2B	0.8600	N4—H4B	0.8600
C1—C2	1.352 (5)	C14—C15	1.388 (5)
C1—H1	0.9300	C15—C16	1.327 (6)
C2—C3	1.381 (5)	C15—H14	0.9300
C2—H2	0.9300	C16—C17	1.382 (5)
C3—C4	1.349 (5)	C16—H15	0.9300
C3—H3	0.9300	C17—C18	1.339 (5)
C4—C5	1.398 (5)	C17—H16	0.9300
C4—H4	0.9300	C18—H18	0.9300
C6—C7	1.501 (5)	C19—C20	1.495 (4)
C7—C8	1.368 (6)	C20—C21	1.380 (5)
C7—C9	1.445 (5)	C20—C22	1.416 (5)
C8—H5	0.9300	C21—H21A	0.9300
C8—H6	0.9300	C21—H21B	0.9300
C9—H7	0.9600	C22—H22A	0.9600
C9—H8	0.9600	C22—H22B	0.9600
C9—H9	0.9600	C22—H22C	0.9600
C10—O8ⁱ	1.249 (4)	C23—O3ⁱⁱ	1.256 (4)
C10—C11	1.508 (4)	C23—C24	1.502 (5)
C11—C12	1.350 (6)	C24—C25	1.351 (5)
C11—C13	1.412 (6)	C24—C26	1.429 (6)
C12—H12A	0.9300	C25—H25A	0.9300
C12—H12B	0.9300	C25—H25B	0.9300
C13—H13A	0.9600	C26—H26A	0.9600
C13—H13B	0.9600	C26—H26B	0.9600
C13—H13C	0.9600	C26—H26C	0.9600

O7—Cu2—O8	167.76 (9)	O3—Cu1—O1ⁱⁱ	90.51 (9)
O7—Cu2—O6	88.23 (9)	O3—Cu1—O4	167.62 (10)
O8—Cu2—O6	89.74 (9)	O1ⁱⁱ—Cu1—O4	88.24 (10)
O7—Cu2—O5ⁱ	90.42 (10)	O3—Cu1—O2	89.23 (9)
O8—Cu2—O5ⁱ	88.94 (9)	O1ⁱⁱ—Cu1—O2	167.56 (9)
O6—Cu2—O5ⁱ	167.47 (10)	O4—Cu1—O2	89.34 (9)
O7—Cu2—N1	98.41 (9)	O3—Cu1—N3	93.68 (10)
O8—Cu2—N1	93.81 (9)	O1ⁱⁱ—Cu1—N3	100.03 (10)
O6—Cu2—N1	96.13 (10)	O4—Cu1—N3	98.67 (10)
O5ⁱ—Cu2—N1	96.39 (10)	O2—Cu1—N3	92.39 (9)
O7—Cu2—Cu2ⁱ	84.33 (7)	O3—Cu1—Cu1ⁱⁱ	83.37 (7)
O8—Cu2—Cu2ⁱ	83.48 (7)	O1ⁱⁱ—Cu1—Cu1ⁱⁱ	83.38 (7)
O6—Cu2—Cu2ⁱ	85.58 (7)	O4—Cu1—Cu1ⁱⁱ	84.24 (7)
O5ⁱ—Cu2—Cu2ⁱ	81.89 (7)	O2—Cu1—Cu1ⁱⁱ	84.24 (7)
N1—Cu2—Cu2ⁱ	176.80 (6)	N3—Cu1—Cu1ⁱⁱ	175.54 (8)
C6—O6—Cu2	121.8 (2)	C19—O2—Cu1	122.8 (2)
C6—O5—Cu2ⁱ	125.4 (2)	C19—O1—Cu1ⁱⁱ	124.1 (2)
C10—O7—Cu2	122.5 (2)	C23—O4—Cu1	122.9 (2)
C10ⁱ—O8—Cu2	123.3 (2)	C23ⁱⁱ—O3—Cu1	124.3 (2)
C1—N1—C5	116.5 (3)	C14—N3—C18	116.5 (3)
C1—N1—Cu2	115.9 (2)	C14—N3—Cu1	127.1 (3)
C5—N1—Cu2	127.5 (3)	C18—N3—Cu1	116.2 (2)
C5—N2—H2A	120.0	C14—N4—H4A	120.0
C5—N2—H2B	120.0	C14—N4—H4B	120.0
H2A—N2—H2B	120.0	H4A—N4—H4B	120.0
N1—C1—C2	125.6 (3)	N4—C14—N3	116.9 (4)
N1—C1—H1	117.2	N4—C14—C15	120.7 (4)
C2—C1—H1	117.2	N3—C14—C15	122.4 (4)
C1—C2—C3	116.9 (4)	C16—C15—C14	118.6 (4)
C1—C2—H2	121.5	C16—C15—H14	120.7
C3—C2—H2	121.5	C14—C15—H14	120.7
C4—C3—C2	120.2 (4)	C15—C16—C17	120.7 (4)
C4—C3—H3	119.9	C15—C16—H15	119.7
C2—C3—H3	119.9	C17—C16—H15	119.7
C3—C4—C5	119.0 (3)	C18—C17—C16	117.5 (4)
C3—C4—H4	120.5	C18—C17—H16	121.3
C5—C4—H4	120.5	C16—C17—H16	121.3
N1—C5—N2	117.6 (3)	C17—C18—N3	124.5 (4)
N1—C5—C4	121.8 (4)	C17—C18—H18	117.8
N2—C5—C4	120.6 (3)	N3—C18—H18	117.8
O6—C6—O5	125.1 (3)	O2—C19—O1	125.3 (3)
O6—C6—C7	117.6 (4)	O2—C19—C20	117.1 (3)
O5—C6—C7	117.2 (3)	O1—C19—C20	117.6 (3)
C8—C7—C9	125.1 (4)	C21—C20—C22	124.5 (3)
C8—C7—C6	117.7 (4)	C21—C20—C19	118.7 (3)
C9—C7—C6	117.2 (4)	C22—C20—C19	116.8 (3)
C7—C8—H5	120.0	C20—C21—H21A	120.0
C7—C8—H6	120.0	C20—C21—H21B	120.0
H5—C8—H6	120.0	H21A—C21—H21B	120.0
C7—C9—H7	109.5	C20—C22—H22A	109.5
C7—C9—H8	109.5	C20—C22—H22B	109.5
H7—C9—H8	109.5	H22A—C22—H22B	109.5
C7—C9—H9	109.5	C20—C22—H22C	109.5
H7—C9—H9	109.5	H22A—C22—H22C	109.5
H8—C9—H9	109.5	H22B—C22—H22C	109.5
O8ⁱ—C10—O7	126.2 (3)	O4—C23—O3ⁱⁱ	125.1 (3)
O8ⁱ—C10—C11	117.1 (3)	O4—C23—C24	117.2 (3)
O7—C10—C11	116.7 (3)	O3ⁱⁱ—C23—C24	117.6 (3)
C12—C11—C13	123.1 (3)	C25—C24—C26	122.6 (4)
C12—C11—C10	119.4 (4)	C25—C24—C23	120.0 (4)
C13—C11—C10	117.4 (4)	C26—C24—C23	117.4 (4)
C11—C12—H12A	120.0	C24—C25—H25A	120.0
C11—C12—H12B	120.0	C24—C25—H25B	120.0
H12A—C12—H12B	120.0	H25A—C25—H25B	120.0
C11—C13—H13A	109.5	C24—C26—H26A	109.5
C11—C13—H13B	109.5	C24—C26—H26B	109.5
H13A—C13—H13B	109.5	H26A—C26—H26B	109.5
C11—C13—H13C	109.5	C24—C26—H26C	109.5
H13A—C13—H13C	109.5	H26A—C26—H26C	109.5
H13B—C13—H13C	109.5	H26B—C26—H26C	109.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5ⁱ	0.86	2.23	2.963 (4)	144
N2—H2B···O2ⁱⁱⁱ	0.86	2.58	3.334 (3)	148
N4—H4A···O4	0.86	2.30	3.051 (4)	145

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

Experimental details

Crystal data
Chemical formula	[Cu₂(C₄H₅O₂)₄(C₅H₆N₂)₂]
M_r	655.64
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	16.8591 (15), 12.1185 (11), 16.5980 (15)
β (°)	117.458 (2)
V (Å³)	3009.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.47
Crystal size (mm)	0.28 × 0.20 × 0.13

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.685, 0.832
No. of measured, independent and observed [I > 2σ(I)] reflections	15356, 5539, 3542
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.084, 0.88
No. of reflections	5539
No. of parameters	365
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.35

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).