Tetra­kis(μ-2-anilinobenzoato)bis­[methano­lcopper(II)](Cu—Cu)

Xin, C.-W.; Liu, F.-C.

doi:10.1107/S1600536808038063

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1589

doi:10.1107/S1600536808038063

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Tetrakis(μ-2-anilinobenzoato)bis[methanolcopper(II)](Cu—Cu)

Chun-Wei Xin ^a and Fu-Chen Liu ^a ^*

^aSchool of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300191, People's Republic of China
^*Correspondence e-mail: fuchenliutj@yahoo.com

(Received 27 October 2008; accepted 16 November 2008; online 22 November 2008)

The title compound, [Cu₂(C₁₃H₁₀NO₂)₄(CH₄O)₂], has been prepared by the reaction of 2-anilinobenzoic acid, HL, with copper(II) nitrate in methanol. This dinuclear complex is arranged around an inversion center. Each Cu atom displays a distorted trigonal–pyramidal coordination with four O atoms from the four ligands L and one axial O atom of the methanol solvent molecule. Each carboxylate group of the ligands L links two Cu atoms, building a dinuclear complex with a Cu—Cu distance of 2.5774 (10) Å. There are intramolecular N—H⋯O hydrogen bonds, and the H atom of the methanol molecule is involved in weak bifurcated hydrogen-bonding interactions with two carboxylate O atoms of related molecules, forming a chain developing parallel to the a axis.

Related literature

For general background, see: Melnik et al. (1998 ); Facchin et al. (1998 ); Martin & Greenwood (1997 ); Moulton et al. (2003 ). For a related structure, see: Churchill et al. (1985 ).

Experimental

Crystal data

[Cu₂(C₁₃H₁₀NO₂)₄(CH₄O)₂]
M_r = 1040.06
Monoclinic, P 2₁ /c
a = 7.2467 (14) Å
b = 14.171 (3) Å
c = 23.813 (5) Å
β = 97.11 (3)°
V = 2426.6 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 293 (2) K
0.22 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
23688 measured reflections
5568 independent reflections
3886 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.115
S = 1.05
5568 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.83	2.04	2.690 (4)	135
N2—H2⋯O3	0.83	2.05	2.688 (4)	133
O5—H5A⋯O1ⁱ	0.84	2.54	3.306 (4)	152
O5—H5A⋯O4ⁱ	0.84	2.55	3.260 (4)	143
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038063/dn2398sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038063/dn2398Isup2.hkl

checkCIF report

Comment top

There is an increasing interest in the design of metal complexes based on polydentate ligands(Martin & Greenwood, 1997). 2-anilinobenzoato and its derivatives with multifunctional sites can bridge metal ions in different mode allowing a large variety of structures (Melnik et al., 1998). In the copper carboxylate based complexes dinuclear tetracarboxylate paddlewheel clusters have been frequently observed (Moulton et al., 2003 and references therein). Several dimer complexes having similar structure to the title complex were reported (Facchin et al., 1998 and references therein).

The dinuclear copper complex is built up around inversion center. Each copper atom displays a trigonal-bipyramidal coordination with four oxygen atoms from the four ligands L and one axial methanol solvent. Each carboxylate groups of the ligands L link two Cu atoms building a dinuclear complex (Fig. 1) with a Cu-Cu distance of 2.5774 (10) Å , typical of tetracarboxylate paddlewheel Cu dinuclear complex(Churchill et al., 1985).

There are intramolecular N-H···O hydrogen bond whereas the H atom of the methanol is in weak bifurcated interactions with two carboxyalte O atoms of related molecule forming a chain developping parallel to the a axis (Table 1).

Related literature top

For general background, see: Melnik et al. (1998); Facchin et al. (1998); Martin & Greenwood (1997); Moulton et al. (2003). For a related structure, see: Churchill et al. (1985).

Experimental top

The title compound was prepared by adding 10 ml of methanol solution of copper nitrate (1 mmol) to 10 ml of methanol solution of L(0.5 mmol) neutralized by sodium aeide(1 mmol). The mixture was stirred for about 2 h and filtered.The filtrate was slowly evaporated at room temperture to yield cubic black crystals of (I) suitable for X-ray analysis. Yield 30% based on copper(II).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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. The molecular structure of the dinuclear complex with the atom-labelling scheme. Ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) -x+2, -y, -z+2]

Tetrakis(µ-2-anilinobenzoato)bis[methanolcopper(II)](Cu—Cu) top

Crystal data top

[Cu₂(C₁₃H₁₀NO₂)₄(CH₄O)₂]	F(000) = 1076
M_r = 1040.06	D_x = 1.423 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19383 reflections
a = 7.2467 (14) Å	θ = 3.0–27.6°
b = 14.171 (3) Å	µ = 0.94 mm⁻¹
c = 23.813 (5) Å	T = 293 K
β = 97.11 (3)°	Block, black
V = 2426.6 (9) Å³	0.22 × 0.20 × 0.15 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	3886 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.073
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −9→9
23688 measured reflections	k = −18→17
5568 independent reflections	l = −30→30

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0338P)² + 2.4261P] where P = (F_o² + 2F_c²)/3
5568 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Cu₂(C₁₃H₁₀NO₂)₄(CH₄O)₂]	V = 2426.6 (9) Å³
M_r = 1040.06	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.2467 (14) Å	µ = 0.94 mm⁻¹
b = 14.171 (3) Å	T = 293 K
c = 23.813 (5) Å	0.22 × 0.20 × 0.15 mm
β = 97.11 (3)°

Data collection top

Bruker SMART CCD diffractometer	3886 reflections with I > 2σ(I)
23688 measured reflections	R_int = 0.073
5568 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.05	Δρ_max = 0.41 e Å⁻³
5568 reflections	Δρ_min = −0.35 e Å⁻³
316 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 > 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	1.13786 (5)	0.05253 (3)	0.990416 (16)	0.02737 (12)
N1	0.9279 (4)	0.2080 (2)	0.83101 (12)	0.0481 (8)
H1	0.9928	0.1944	0.8612	0.058*
N2	1.0262 (4)	0.3315 (2)	1.06884 (14)	0.0492 (8)
H2	1.0768	0.2917	1.0500	0.059*
O1	0.7459 (3)	0.00204 (19)	0.93852 (11)	0.0549 (7)
O2	0.9804 (3)	0.09287 (18)	0.92135 (9)	0.0424 (6)
O3	1.0252 (3)	0.15225 (16)	1.03190 (10)	0.0436 (6)
O4	0.7885 (3)	0.06096 (16)	1.04750 (12)	0.0532 (7)
O5	1.3926 (3)	0.12326 (16)	0.97707 (10)	0.0460 (6)
H5A	1.4998	0.0999	0.9789	0.055*
C1	0.8163 (4)	0.0628 (2)	0.90930 (13)	0.0319 (7)
C2	0.6955 (4)	0.0996 (2)	0.85929 (13)	0.0311 (7)
C3	0.5154 (5)	0.0638 (2)	0.84879 (14)	0.0404 (8)
H3	0.4795	0.0165	0.8723	0.049*
C4	0.3890 (5)	0.0955 (3)	0.80525 (16)	0.0502 (10)
H4	0.2712	0.0688	0.7983	0.060*
C5	0.4416 (5)	0.1681 (3)	0.77200 (16)	0.0536 (11)
H5	0.3564	0.1922	0.7432	0.064*
C6	0.6177 (5)	0.2053 (3)	0.78080 (15)	0.0473 (10)
H6	0.6491	0.2544	0.7578	0.057*
C7	0.7506 (4)	0.1714 (2)	0.82325 (14)	0.0354 (8)
C8	1.0119 (5)	0.2737 (2)	0.79817 (15)	0.0391 (8)
C9	1.1365 (5)	0.3380 (3)	0.82540 (16)	0.0464 (9)
H9	1.1578	0.3381	0.8647	0.056*
C10	1.2290 (6)	0.4012 (3)	0.7956 (2)	0.0625 (12)
H10	1.3126	0.4435	0.8147	0.075*
C11	1.1986 (7)	0.4023 (4)	0.7379 (2)	0.0776 (15)
H11	1.2604	0.4456	0.7175	0.093*
C12	1.0764 (6)	0.3393 (4)	0.71023 (19)	0.0752 (15)
H12	1.0554	0.3403	0.6709	0.090*
C13	0.9836 (5)	0.2743 (3)	0.73948 (16)	0.0544 (11)
H13	0.9027	0.2312	0.7200	0.065*
C14	0.8729 (4)	0.1384 (2)	1.05159 (13)	0.0323 (7)
C15	0.7840 (4)	0.2162 (2)	1.07961 (13)	0.0308 (7)
C16	0.6150 (5)	0.1969 (3)	1.10022 (14)	0.0395 (8)
H16	0.5680	0.1358	1.0971	0.047*
C17	0.5161 (5)	0.2646 (3)	1.12476 (16)	0.0454 (9)
H17	0.4044	0.2499	1.1382	0.055*
C18	0.5858 (5)	0.3544 (3)	1.12903 (16)	0.0485 (10)
H18	0.5195	0.4013	1.1451	0.058*
C19	0.7510 (5)	0.3763 (2)	1.11009 (16)	0.0441 (9)
H19	0.7934	0.4383	1.1130	0.053*
C20	0.8583 (4)	0.3083 (2)	1.08640 (14)	0.0353 (8)
C21	1.1236 (5)	0.4172 (2)	1.08019 (18)	0.0446 (9)
C22	1.2051 (5)	0.4608 (3)	1.03751 (19)	0.0583 (11)
H22	1.1940	0.4345	1.0015	0.070*
C23	1.3035 (6)	0.5441 (3)	1.0488 (2)	0.0743 (14)
H23	1.3570	0.5738	1.0200	0.089*
C24	1.3229 (6)	0.5830 (3)	1.1018 (3)	0.0756 (15)
H24	1.3891	0.6388	1.1089	0.091*
C25	1.2444 (6)	0.5391 (3)	1.1442 (2)	0.0630 (12)
H25	1.2570	0.5656	1.1802	0.076*
C26	1.1472 (5)	0.4564 (3)	1.13402 (18)	0.0520 (10)
H26	1.0968	0.4264	1.1634	0.062*
C27	1.4132 (6)	0.2166 (3)	0.95906 (19)	0.0658 (12)
H27A	1.5422	0.2292	0.9568	0.099*
H27B	1.3682	0.2592	0.9856	0.099*
H27C	1.3433	0.2252	0.9225	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0269 (2)	0.0242 (2)	0.0313 (2)	−0.00364 (18)	0.00475 (14)	0.00085 (17)
N1	0.0402 (18)	0.061 (2)	0.0409 (18)	−0.0093 (16)	−0.0023 (14)	0.0202 (15)
N2	0.0371 (17)	0.0344 (17)	0.080 (2)	−0.0060 (14)	0.0218 (16)	−0.0171 (16)
O1	0.0446 (15)	0.0644 (18)	0.0516 (16)	−0.0184 (14)	−0.0104 (12)	0.0285 (14)
O2	0.0358 (14)	0.0535 (15)	0.0366 (14)	−0.0067 (12)	−0.0015 (11)	0.0123 (12)
O3	0.0407 (14)	0.0362 (14)	0.0571 (16)	−0.0074 (12)	0.0189 (12)	−0.0157 (12)
O4	0.0511 (16)	0.0295 (14)	0.085 (2)	−0.0092 (13)	0.0326 (14)	−0.0149 (13)
O5	0.0321 (13)	0.0390 (14)	0.0679 (18)	−0.0078 (11)	0.0098 (12)	0.0084 (13)
C1	0.0351 (19)	0.0304 (18)	0.0307 (17)	0.0024 (16)	0.0060 (14)	−0.0032 (15)
C2	0.0326 (18)	0.0308 (18)	0.0304 (17)	0.0025 (15)	0.0059 (14)	−0.0027 (14)
C3	0.038 (2)	0.042 (2)	0.041 (2)	−0.0035 (17)	0.0059 (16)	0.0038 (17)
C4	0.032 (2)	0.068 (3)	0.049 (2)	−0.0077 (19)	−0.0012 (17)	0.006 (2)
C5	0.037 (2)	0.077 (3)	0.045 (2)	0.009 (2)	−0.0025 (17)	0.017 (2)
C6	0.041 (2)	0.056 (2)	0.045 (2)	0.0051 (19)	0.0051 (17)	0.0188 (18)
C7	0.0319 (19)	0.040 (2)	0.0345 (19)	0.0012 (16)	0.0052 (14)	0.0004 (15)
C8	0.0348 (19)	0.040 (2)	0.042 (2)	0.0010 (17)	0.0046 (16)	0.0095 (16)
C9	0.046 (2)	0.047 (2)	0.045 (2)	−0.0055 (19)	0.0005 (17)	−0.0036 (18)
C10	0.053 (3)	0.046 (3)	0.088 (4)	−0.013 (2)	0.006 (2)	0.003 (2)
C11	0.064 (3)	0.083 (4)	0.085 (4)	−0.021 (3)	0.006 (3)	0.044 (3)
C12	0.055 (3)	0.120 (4)	0.048 (3)	−0.018 (3)	0.000 (2)	0.035 (3)
C13	0.042 (2)	0.074 (3)	0.046 (2)	−0.017 (2)	0.0003 (18)	0.010 (2)
C14	0.0312 (18)	0.0302 (19)	0.0347 (19)	−0.0006 (15)	0.0004 (14)	−0.0009 (14)
C15	0.0272 (17)	0.0312 (18)	0.0335 (18)	0.0007 (14)	0.0014 (14)	−0.0026 (14)
C16	0.039 (2)	0.035 (2)	0.045 (2)	−0.0044 (16)	0.0083 (16)	−0.0021 (16)
C17	0.035 (2)	0.045 (2)	0.060 (2)	−0.0055 (18)	0.0168 (18)	−0.0112 (19)
C18	0.033 (2)	0.047 (2)	0.066 (3)	0.0111 (18)	0.0081 (18)	−0.014 (2)
C19	0.035 (2)	0.0287 (19)	0.068 (3)	0.0007 (16)	0.0032 (18)	−0.0070 (17)
C20	0.0268 (18)	0.0327 (19)	0.046 (2)	0.0006 (15)	0.0031 (15)	−0.0048 (16)
C21	0.0280 (19)	0.0310 (19)	0.075 (3)	−0.0015 (16)	0.0094 (18)	−0.0045 (18)
C22	0.047 (2)	0.052 (3)	0.074 (3)	−0.005 (2)	0.003 (2)	0.006 (2)
C23	0.058 (3)	0.056 (3)	0.107 (4)	−0.018 (2)	0.003 (3)	0.027 (3)
C24	0.057 (3)	0.037 (2)	0.128 (5)	−0.011 (2)	−0.007 (3)	−0.003 (3)
C25	0.043 (2)	0.048 (3)	0.096 (4)	0.000 (2)	0.001 (2)	−0.023 (2)
C26	0.037 (2)	0.044 (2)	0.077 (3)	−0.0041 (19)	0.0122 (19)	−0.012 (2)
C27	0.074 (3)	0.046 (2)	0.077 (3)	−0.016 (2)	0.007 (2)	0.014 (2)

Geometric parameters (Å, º) top

Cu1—O4ⁱ	1.951 (2)	C9—H9	0.9300
Cu1—O1ⁱ	1.954 (2)	C10—C11	1.365 (6)
Cu1—O3	1.959 (2)	C10—H10	0.9300
Cu1—O2	1.967 (2)	C11—C12	1.367 (6)
Cu1—O5	2.159 (2)	C11—H11	0.9300
Cu1—Cu1ⁱ	2.5774 (10)	C12—C13	1.379 (5)
N1—C7	1.377 (4)	C12—H12	0.9300
N1—C8	1.402 (4)	C13—H13	0.9300
N1—H1	0.8314	C14—C15	1.477 (4)
N2—C20	1.375 (4)	C15—C16	1.402 (4)
N2—C21	1.413 (4)	C15—C20	1.413 (4)
N2—H2	0.8323	C16—C17	1.371 (5)
O1—C1	1.254 (4)	C16—H16	0.9300
O1—Cu1ⁱ	1.954 (2)	C17—C18	1.368 (5)
O2—C1	1.263 (4)	C17—H17	0.9300
O3—C14	1.266 (4)	C18—C19	1.366 (5)
O4—C14	1.255 (4)	C18—H18	0.9300
O4—Cu1ⁱ	1.951 (2)	C19—C20	1.400 (5)
O5—C27	1.404 (4)	C19—H19	0.9300
O5—H5A	0.8409	C21—C22	1.383 (5)
C1—C2	1.483 (4)	C21—C26	1.388 (5)
C2—C3	1.394 (5)	C22—C23	1.387 (6)
C2—C7	1.420 (4)	C22—H22	0.9300
C3—C4	1.371 (5)	C23—C24	1.368 (7)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.380 (5)	C24—C25	1.369 (6)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.373 (5)	C25—C26	1.374 (5)
C5—H5	0.9300	C25—H25	0.9300
C6—C7	1.392 (5)	C26—H26	0.9300
C6—H6	0.9300	C27—H27A	0.9600
C8—C9	1.386 (5)	C27—H27B	0.9600
C8—C13	1.387 (5)	C27—H27C	0.9600
C9—C10	1.369 (5)

O4ⁱ—Cu1—O1ⁱ	87.77 (12)	C11—C10—H10	120.0
O4ⁱ—Cu1—O3	169.37 (10)	C9—C10—H10	120.0
O1ⁱ—Cu1—O3	90.61 (12)	C10—C11—C12	119.4 (4)
O4ⁱ—Cu1—O2	90.93 (12)	C10—C11—H11	120.3
O1ⁱ—Cu1—O2	169.23 (10)	C12—C11—H11	120.3
O3—Cu1—O2	88.69 (11)	C11—C12—C13	121.3 (4)
O4ⁱ—Cu1—O5	91.53 (10)	C11—C12—H12	119.3
O1ⁱ—Cu1—O5	91.52 (10)	C13—C12—H12	119.3
O3—Cu1—O5	99.02 (10)	C12—C13—C8	119.6 (4)
O2—Cu1—O5	99.21 (10)	C12—C13—H13	120.2
O4ⁱ—Cu1—Cu1ⁱ	82.43 (8)	C8—C13—H13	120.2
O1ⁱ—Cu1—Cu1ⁱ	83.02 (8)	O4—C14—O3	123.1 (3)
O3—Cu1—Cu1ⁱ	86.94 (7)	O4—C14—C15	116.9 (3)
O2—Cu1—Cu1ⁱ	86.21 (7)	O3—C14—C15	120.0 (3)
O5—Cu1—Cu1ⁱ	171.98 (7)	C16—C15—C20	118.5 (3)
C7—N1—C8	129.6 (3)	C16—C15—C14	117.5 (3)
C7—N1—H1	116.6	C20—C15—C14	124.0 (3)
C8—N1—H1	113.4	C17—C16—C15	122.6 (3)
C20—N2—C21	125.9 (3)	C17—C16—H16	118.7
C20—N2—H2	117.8	C15—C16—H16	118.7
C21—N2—H2	116.2	C18—C17—C16	118.4 (3)
C1—O1—Cu1ⁱ	126.2 (2)	C18—C17—H17	120.8
C1—O2—Cu1	121.6 (2)	C16—C17—H17	120.8
C14—O3—Cu1	120.8 (2)	C19—C18—C17	121.2 (3)
C14—O4—Cu1ⁱ	126.8 (2)	C19—C18—H18	119.4
C27—O5—Cu1	127.4 (2)	C17—C18—H18	119.4
C27—O5—H5A	104.8	C18—C19—C20	122.0 (3)
Cu1—O5—H5A	127.6	C18—C19—H19	119.0
O1—C1—O2	122.8 (3)	C20—C19—H19	119.0
O1—C1—C2	116.5 (3)	N2—C20—C19	121.0 (3)
O2—C1—C2	120.6 (3)	N2—C20—C15	121.7 (3)
C3—C2—C7	118.6 (3)	C19—C20—C15	117.3 (3)
C3—C2—C1	117.6 (3)	C22—C21—C26	119.0 (4)
C7—C2—C1	123.7 (3)	C22—C21—N2	119.5 (4)
C4—C3—C2	122.6 (3)	C26—C21—N2	121.5 (4)
C4—C3—H3	118.7	C21—C22—C23	119.6 (4)
C2—C3—H3	118.7	C21—C22—H22	120.2
C3—C4—C5	118.2 (3)	C23—C22—H22	120.2
C3—C4—H4	120.9	C24—C23—C22	120.9 (5)
C5—C4—H4	120.9	C24—C23—H23	119.6
C6—C5—C4	121.1 (3)	C22—C23—H23	119.6
C6—C5—H5	119.5	C23—C24—C25	119.6 (4)
C4—C5—H5	119.5	C23—C24—H24	120.2
C5—C6—C7	121.6 (4)	C25—C24—H24	120.2
C5—C6—H6	119.2	C24—C25—C26	120.5 (5)
C7—C6—H6	119.2	C24—C25—H25	119.7
N1—C7—C6	121.1 (3)	C26—C25—H25	119.7
N1—C7—C2	121.1 (3)	C25—C26—C21	120.4 (4)
C6—C7—C2	117.7 (3)	C25—C26—H26	119.8
C9—C8—C13	118.2 (3)	C21—C26—H26	119.8
C9—C8—N1	118.5 (3)	O5—C27—H27A	109.5
C13—C8—N1	123.1 (3)	O5—C27—H27B	109.5
C10—C9—C8	121.4 (4)	H27A—C27—H27B	109.5
C10—C9—H9	119.3	O5—C27—H27C	109.5
C8—C9—H9	119.3	H27A—C27—H27C	109.5
C11—C10—C9	120.1 (4)	H27B—C27—H27C	109.5

Symmetry code: (i) −x+2, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.83	2.04	2.690 (4)	135
N2—H2···O3	0.83	2.05	2.688 (4)	133
O5—H5A···O1ⁱⁱ	0.84	2.54	3.306 (4)	152
O5—H5A···O4ⁱⁱ	0.84	2.55	3.260 (4)	143

Symmetry code: (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₃H₁₀NO₂)₄(CH₄O)₂]
M_r	1040.06
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.2467 (14), 14.171 (3), 23.813 (5)
β (°)	97.11 (3)
V (Å³)	2426.6 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.22 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	23688, 5568, 3886
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.115, 1.05
No. of reflections	5568
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.35

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.83	2.04	2.690 (4)	134.5
N2—H2···O3	0.83	2.05	2.688 (4)	133.3
O5—H5A···O1ⁱ	0.84	2.54	3.306 (4)	152.0
O5—H5A···O4ⁱ	0.84	2.55	3.260 (4)	142.9

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors acknowledge financial support from Tianjin Municipal Education Commission (grant No. 20060503)

References

Bruker (1998). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Churchill, M. R., Li, Y.-J., Nalewajek, D., Schaber, P. M. & Dorfamanii, J. (1985). Inorg. Chem. 24, 2684–2687. CSD CrossRef CAS Web of Science Google Scholar
Facchin, G., Torre, M. H., Kremer, E., Piro, O. E. & Baran, E. J. (1998). Z. Anorg. Allg. Chem. 53, 871–874. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Martin, J. D. & Greenwood, K. B. (1997). Angew. Chem. Int. Ed. 36, 2072–2075. CrossRef CAS Google Scholar
Melnik, M., Koman, M. & Glowiak, T. (1998). Polyhedron, 17, 1767–1771. Web of Science CSD CrossRef CAS Google Scholar
Moulton, B., Abourahma, H., Bradner, M. W., Lu, J.-J., McManus, G. J. & Zaworotko, M. J. (2003). Chem. Commun. pp. 1342–1343. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar