Bis(μ-2,2′-{[4-(carb­oxy­meth­oxy)phen­yl]aza­nedi­yl}diacetato)­bis­[(1,10-phenanthroline)copper(II)]

Zhao, Y.; Pan, T.; Chen, Z.

doi:10.1107/S1600536810048488

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages m1670-m1671

https://doi.org/10.1107/S1600536810048488

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Bis(μ-2,2′-{[4-(carboxymethoxy)phenyl]azanediyl}diacetato)bis[(1,10-phenanthroline)copper(II)]

Yan Zhao,^a ^* Tonghen Pan ^b and Zhitao Chen ^c

^aCollege of Life Science, Fujian Agriculture and Forestry University, Fuzhou, Fujian 350002, People's Republic of China, ^bDepartment of Chemistry, Fuzhou University, Fuzhou, Fujian 350108, People's Republic of China, and ^cFuqing Entry–exit Inspection and Quarantine Bureau, Fuqing, Fujian 350300, People's Republic of China
^*Correspondence e-mail: zy13054518939@yahoo.com.cn

(Received 19 November 2010; accepted 21 November 2010; online 27 November 2010)

The crystal structure of the binuclear title compound, [Cu₂(C₁₂H₁₁NO₇)₂(C₁₂H₈N₂)₂], consists of a complex molecule, which lies about a crystallographic inversion centre with one half-molecule in the asymmetric unit. The Cu^II cation is bonded to three N atoms and three O atoms, in a Jahn–Teller-distorted octahedral geometry. The basal plane is defined by the two N atoms from the 1,10-phenathroline and two deprotonated O atoms of the polycarboxylate ligand. The axial positions are occupied by the azane N atom and a bridging carboxylate O atom from the second polycarboxylate ligand. The complex molecules are linked through O—H⋯O hydrogen bonds into extended chains running parallel to [010].

Related literature

For general background to the applications of polycarboxylate ligands, see: Ghermani et al. (1994 ); Ruiz-Perez et al. (2000 ); Ye et al. (2005 ); Kido et al. (2003 ). For the features of flexible multidentate aromatic polycarboxylate ligands, see: Wang et al. (2009 ); Pan et al. (2008 ); Dong et al. (2006 ).

Experimental

Crystal data

[Cu₂(C₁₂H₁₁NO₇)₂(C₁₂H₈N₂)₂]
M_r = 1049.92
Monoclinic, P 2₁ /c
a = 8.7410 (17) Å
b = 10.886 (2) Å
c = 22.239 (4) Å
β = 90.85 (3)°
V = 2115.8 (7) Å³
Z = 2
Mo Kα radiation
μ = 1.09 mm⁻¹
T = 293 K
0.26 × 0.18 × 0.12 mm

Data collection

Rigaku Mercury CCD area-detector diffractometer
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 1998 ) T_min = 0.85, T_max = 1.00
14139 measured reflections
3604 independent reflections
3408 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.103
S = 1.25
3604 reflections
317 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—O7	1.987 (3)
Cu1—O5	1.997 (3)
Cu1—N2	2.003 (3)
Cu1—N3	2.049 (3)
Cu1—O7ⁱ	2.293 (3)
Cu1—N1	2.460 (3)

O7—Cu1—O5	92.08 (11)
O7—Cu1—N2	171.29 (12)
O5—Cu1—N2	93.61 (12)
O7—Cu1—N3	91.96 (12)
O5—Cu1—N3	170.40 (12)
N2—Cu1—N3	81.44 (13)
O7—Cu1—O7ⁱ	77.11 (11)
O5—Cu1—O7ⁱ	93.01 (10)
N2—Cu1—O7ⁱ	109.13 (11)
N3—Cu1—O7ⁱ	96.38 (11)
O7—Cu1—N1	74.69 (11)
O5—Cu1—N1	76.84 (11)
N2—Cu1—N1	100.21 (12)
N3—Cu1—N1	95.87 (12)
O7ⁱ—Cu1—N1	149.54 (10)
Symmetry code: (i) -x, -y, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4ⁱⁱ	0.82	1.82	2.622 (4)	164
Symmetry code: (ii) x, y+1, z.

Data collection: CrystalClear (Rigaku, 2002 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810048488/sj5063sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048488/sj5063Isup2.hkl

checkCIF report

Comment top

Carboxylate-metal coordination compounds have received considerable attention due to their potential applications in catalysis and pharmaceutical chemistry (Ghermani et al., 1994; Ruiz-Perez et al., 2000), molecular recognition and magnetic materials (Ye et al., 2005); Kido, et al., 2003). In recent years, several studies have focused on flexible multidentate aromatic polycarboxylate ligands, because of their remarkable features. These ligands contain carboxylate groups, which can provide a variety of coordination modes (Wang et al., 2009). They also offer the opportunity to form hydrogen bonds leading to supramolecular structures (Pan et al., 2008). Furthermore, such ligands can be used to construct unprecedented topological frameworks (Dong et al., 2006). Here, we present the structure of the title compound (I), a copper complex with 2,2'-(4-(carboxymethoxy)phenylazanediyl)diacetate, a flexible multidentate aromatic polycarboxylate ligand.

As shown in Fig. 1, the binuclear complex contains two Cu^II cations with very distorted octahedral geometries. The basal plane of each coordination site is defined by the N2 and N3 atoms from the 1,10-phenathroline ligand and the deprotanated O5 and O7 atoms from a polycarboxylate ligand. The axial positions are occupied by the azane N1 atom and a bridging O7A atom from the second polycarboxylate ligand. The angle O7A—Cu1—N1 and the axial bond lengths are respectively 149.54 (10)°; Cu1—O7A, 2.293 (3)Å; Cu1—N1, 2.460 (3)Å which demonstrate a very distorted octahedral coordination geometry due to the Jahn-Teller effect. The packing is stabilized through intermolecular hydrogen-bonding between the uncoordinated carboxyl O—H group and a neighboring carbonyl oxygen atom. This results in a 1-dimensional hydrogen-bonded chain parallel to the [010] direction (Fig. 2 and Table 1).

Related literature top

For general background to the applications of polycarboxylate ligands, see: Ghermani et al. (1994); Ruiz-Perez et al. (2000); Ye et al. (2005); Kido et al. (2003). For the features of flexible multidentate aromatic polycarboxylate ligands, see: Wang et al. (2009); Pan et al. (2008); Dong et al. (2006).

Experimental top

The polycarboxylate ligand (0.082 g, 0.3 mmol), Cu(CH₃COO)₂.2H₂O (0.044 g, 0.2 mmol) and 1,10-phenathroline (0.055 g, 0.3 mmol) were dissolved in a mixed solvent of ethanol and water (8 ml, 5:3 v/v) and stirred for 4 h at room temperature. The mixture was filtered and allowed to evaporate in air at room temperature. Block-like blue crystals separated from the filtrate after 8 days.

Structure description top

For general background to the applications of polycarboxylate ligands, see: Ghermani et al. (1994); Ruiz-Perez et al. (2000); Ye et al. (2005); Kido et al. (2003). For the features of flexible multidentate aromatic polycarboxylate ligands, see: Wang et al. (2009); Pan et al. (2008); Dong et al. (2006).

Computing details top

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear (Rigaku, 2002; data reduction: CrystalClear (Rigaku, 2002; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound with 30% probability displacement ellipsoids. The weak axial Cu—N bonds are shown as dashed lines. H atoms have been omitted for clarity. [Atoms labelled with the suffix A are related to other atoms by the symmetry code: [-x,-y,-z]
	Fig. 2. A view of the hydrogen-bonded 1-dimensional chains running parallel to [010]. The hydrogen bonds are shown as dashed lines.

Bis(µ-2,2'-{[4-(carboxymethoxy)phenyl]azanediyl}diacetato)bis[(1,10- phenanthroline)copper(II)] top

Crystal data top

[Cu₂(C₁₂H₁₁NO₇)₂(C₁₂H₈N₂)₂]	F(000) = 1076
M_r = 1049.92	D_x = 1.648 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.7410 (17) Å	θ = 12–18°
b = 10.886 (2) Å	µ = 1.09 mm⁻¹
c = 22.239 (4) Å	T = 293 K
β = 90.85 (3)°	Block, blue
V = 2115.8 (7) Å³	0.26 × 0.18 × 0.12 mm
Z = 2

Data collection top

Rigaku Mercury CCD area-detector diffractometer	3604 independent reflections
Radiation source: fine-focus sealed tube	3408 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ω scans	θ_max = 24.7°, θ_min = 3.1°
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 1998)	h = −10→10
T_min = 0.85, T_max = 1.00	k = −12→12
14139 measured reflections	l = −26→26

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) = 0.103	H-atom parameters constrained
S = 1.25	w = 1/[σ²(F_o²) + (0.0128P)² + 3.5126P] where P = (F_o² + 2F_c²)/3
3604 reflections	(Δ/σ)_max = 0.001
317 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Cu₂(C₁₂H₁₁NO₇)₂(C₁₂H₈N₂)₂]	V = 2115.8 (7) Å³
M_r = 1049.92	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.7410 (17) Å	µ = 1.09 mm⁻¹
b = 10.886 (2) Å	T = 293 K
c = 22.239 (4) Å	0.26 × 0.18 × 0.12 mm
β = 90.85 (3)°

Data collection top

Rigaku Mercury CCD area-detector diffractometer	3604 independent reflections
Absorption correction: multi-scan (RAPID-AUTO; Rigaku, 1998)	3408 reflections with I > 2σ(I)
T_min = 0.85, T_max = 1.00	R_int = 0.052
14139 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.25	Δρ_max = 0.27 e Å⁻³
3604 reflections	Δρ_min = −0.35 e Å⁻³
317 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	0.05701 (5)	0.10839 (4)	0.04897 (2)	0.03031 (15)
O5	−0.0341 (3)	0.0219 (2)	0.11910 (12)	0.0356 (7)
O7	0.1363 (3)	−0.0478 (2)	0.01526 (12)	0.0326 (6)
N1	0.2819 (4)	0.0561 (3)	0.11173 (14)	0.0304 (7)
N2	0.0092 (4)	0.2758 (3)	0.08106 (15)	0.0319 (8)
N3	0.1739 (4)	0.2109 (3)	−0.01248 (15)	0.0330 (8)
O6	0.3412 (3)	−0.1600 (3)	−0.00516 (14)	0.0459 (8)
O2	0.1572 (4)	0.7030 (3)	0.24279 (14)	0.0528 (9)
H2	0.1176	0.7503	0.2184	0.063*
O3	0.4623 (4)	0.4841 (3)	0.23479 (15)	0.0550 (9)
O1	0.3190 (4)	0.6653 (3)	0.16736 (15)	0.0605 (9)
O4	−0.0057 (3)	−0.1359 (3)	0.18195 (14)	0.0500 (8)
C1	0.2762 (5)	0.6474 (4)	0.2177 (2)	0.0434 (11)
C2	0.3508 (6)	0.5602 (4)	0.2620 (2)	0.0546 (13)
H2A	0.3991	0.6073	0.2941	0.066*
H2B	0.2728	0.5089	0.2798	0.066*
C3	0.4095 (5)	0.3800 (4)	0.2047 (2)	0.0401 (10)
C4	0.2869 (5)	0.3104 (4)	0.2226 (2)	0.0482 (12)
H4	0.2304	0.3347	0.2557	0.058*
C5	0.2476 (5)	0.2047 (4)	0.19176 (19)	0.0432 (11)
H5	0.1638	0.1593	0.2043	0.052*
C6	0.3299 (4)	0.1642 (4)	0.14239 (17)	0.0291 (9)
C7	0.4531 (4)	0.2351 (4)	0.12463 (18)	0.0335 (9)
H7	0.5100	0.2110	0.0917	0.040*
C8	0.4928 (5)	0.3423 (4)	0.15567 (19)	0.0377 (10)
H8	0.5759	0.3888	0.1432	0.045*
C9	0.2205 (4)	−0.0419 (4)	0.14958 (18)	0.0349 (10)
H9A	0.2570	−0.0290	0.1905	0.042*
H9B	0.2618	−0.1197	0.1360	0.042*
C10	0.0478 (5)	−0.0518 (4)	0.15017 (18)	0.0342 (10)
C11	0.3746 (4)	0.0071 (4)	0.06312 (18)	0.0325 (9)
H11A	0.4592	−0.0398	0.0801	0.039*
H11B	0.4168	0.0745	0.0402	0.039*
C12	0.2791 (5)	−0.0758 (4)	0.02112 (18)	0.0327 (9)
C13	0.2498 (4)	0.1765 (4)	−0.06094 (19)	0.0378 (10)
H13	0.2383	0.0963	−0.0746	0.045*
C14	0.3463 (5)	0.2557 (4)	−0.0924 (2)	0.0452 (11)
H14	0.3974	0.2285	−0.1262	0.054*
C15	0.3644 (5)	0.3735 (4)	−0.0725 (2)	0.0466 (12)
H15	0.4320	0.4259	−0.0918	0.056*
C16	0.2812 (5)	0.4161 (4)	−0.02308 (19)	0.0381 (10)
C17	0.1868 (4)	0.3301 (4)	0.00554 (18)	0.0317 (9)
C18	0.0961 (4)	0.3654 (4)	0.05541 (18)	0.0336 (10)
C19	0.0966 (5)	0.4885 (4)	0.0753 (2)	0.0378 (10)
C20	0.1934 (5)	0.5738 (4)	0.0444 (2)	0.0487 (12)
H20	0.1951	0.6554	0.0568	0.058*
C21	0.2807 (5)	0.5397 (4)	−0.0012 (2)	0.0465 (12)
H21	0.3430	0.5978	−0.0193	0.056*
C22	0.0007 (5)	0.5157 (4)	0.1236 (2)	0.0452 (11)
H22	−0.0044	0.5955	0.1383	0.054*
C23	−0.0846 (5)	0.4261 (4)	0.1489 (2)	0.0475 (12)
H23	−0.1471	0.4445	0.1812	0.057*
C24	−0.0788 (5)	0.3064 (4)	0.12670 (19)	0.0407 (10)
H24	−0.1386	0.2462	0.1445	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0304 (3)	0.0260 (3)	0.0346 (3)	−0.0016 (2)	0.0050 (2)	0.0013 (2)
O5	0.0316 (15)	0.0351 (16)	0.0403 (17)	0.0001 (13)	0.0064 (13)	0.0070 (13)
O7	0.0301 (16)	0.0294 (15)	0.0383 (16)	−0.0020 (12)	0.0024 (12)	−0.0052 (12)
N1	0.0304 (18)	0.0289 (18)	0.0320 (18)	−0.0030 (15)	0.0074 (14)	0.0003 (15)
N2	0.0305 (18)	0.0294 (18)	0.0358 (19)	0.0004 (15)	−0.0009 (15)	0.0044 (15)
N3	0.0286 (18)	0.0318 (19)	0.039 (2)	−0.0017 (15)	0.0023 (15)	0.0029 (15)
O6	0.0423 (18)	0.0338 (17)	0.062 (2)	−0.0010 (14)	0.0179 (15)	−0.0130 (15)
O2	0.064 (2)	0.053 (2)	0.0415 (19)	0.0204 (17)	0.0086 (16)	0.0072 (16)
O3	0.048 (2)	0.0419 (18)	0.075 (2)	0.0052 (16)	−0.0136 (17)	−0.0256 (17)
O1	0.072 (2)	0.060 (2)	0.050 (2)	0.0073 (19)	0.0139 (18)	0.0041 (18)
O4	0.0411 (18)	0.0484 (19)	0.061 (2)	−0.0050 (15)	0.0101 (15)	0.0244 (16)
C1	0.053 (3)	0.033 (2)	0.044 (3)	−0.003 (2)	−0.002 (2)	−0.007 (2)
C2	0.064 (3)	0.044 (3)	0.056 (3)	0.013 (2)	−0.016 (3)	−0.018 (2)
C3	0.038 (2)	0.034 (2)	0.048 (3)	0.002 (2)	−0.011 (2)	−0.008 (2)
C4	0.037 (2)	0.059 (3)	0.049 (3)	−0.001 (2)	0.004 (2)	−0.022 (2)
C5	0.034 (2)	0.053 (3)	0.044 (3)	−0.013 (2)	0.0040 (19)	−0.011 (2)
C6	0.024 (2)	0.031 (2)	0.032 (2)	−0.0003 (17)	−0.0007 (16)	0.0014 (18)
C7	0.032 (2)	0.032 (2)	0.037 (2)	0.0009 (18)	0.0025 (18)	0.0010 (18)
C8	0.039 (2)	0.029 (2)	0.045 (3)	−0.0052 (19)	−0.003 (2)	0.004 (2)
C9	0.033 (2)	0.037 (2)	0.035 (2)	−0.0031 (18)	0.0012 (18)	0.0068 (19)
C10	0.035 (2)	0.035 (2)	0.033 (2)	−0.005 (2)	0.0054 (18)	0.0002 (19)
C11	0.025 (2)	0.031 (2)	0.042 (2)	0.0012 (17)	0.0034 (17)	0.0002 (18)
C12	0.033 (2)	0.025 (2)	0.040 (2)	−0.0044 (18)	0.0132 (18)	0.0025 (18)
C13	0.033 (2)	0.039 (2)	0.042 (2)	−0.0031 (19)	0.0045 (19)	0.004 (2)
C14	0.041 (3)	0.050 (3)	0.045 (3)	0.003 (2)	0.008 (2)	0.011 (2)
C15	0.033 (2)	0.050 (3)	0.056 (3)	−0.006 (2)	0.005 (2)	0.016 (2)
C16	0.035 (2)	0.032 (2)	0.047 (3)	−0.0062 (19)	−0.009 (2)	0.014 (2)
C17	0.027 (2)	0.030 (2)	0.038 (2)	−0.0023 (17)	−0.0051 (17)	0.0051 (19)
C18	0.031 (2)	0.032 (2)	0.037 (2)	−0.0028 (18)	−0.0089 (18)	0.0046 (18)
C19	0.036 (2)	0.031 (2)	0.046 (3)	−0.0014 (19)	−0.0115 (19)	0.001 (2)
C20	0.057 (3)	0.030 (2)	0.059 (3)	−0.010 (2)	−0.017 (3)	0.002 (2)
C21	0.044 (3)	0.038 (3)	0.058 (3)	−0.013 (2)	−0.006 (2)	0.009 (2)
C22	0.045 (3)	0.035 (3)	0.056 (3)	0.002 (2)	−0.011 (2)	−0.009 (2)
C23	0.050 (3)	0.049 (3)	0.044 (3)	0.010 (2)	−0.002 (2)	−0.009 (2)
C24	0.038 (2)	0.042 (3)	0.042 (3)	0.002 (2)	0.003 (2)	0.002 (2)

Geometric parameters (Å, º) top

Cu1—O7	1.987 (3)	C5—H5	0.9300
Cu1—O5	1.997 (3)	C6—C7	1.387 (5)
Cu1—N2	2.003 (3)	C7—C8	1.397 (6)
Cu1—N3	2.049 (3)	C7—H7	0.9300
Cu1—O7ⁱ	2.293 (3)	C8—H8	0.9300
Cu1—N1	2.460 (3)	C9—C10	1.514 (5)
O5—C10	1.272 (5)	C9—H9A	0.9700
O7—C12	1.290 (5)	C9—H9B	0.9700
O7—Cu1ⁱ	2.293 (3)	C11—C12	1.536 (5)
N1—C6	1.420 (5)	C11—H11A	0.9700
N1—C11	1.462 (5)	C11—H11B	0.9700
N1—C9	1.465 (5)	C13—C14	1.401 (6)
N2—C24	1.325 (5)	C13—H13	0.9300
N2—C18	1.366 (5)	C14—C15	1.364 (6)
N3—C13	1.327 (5)	C14—H14	0.9300
N3—C17	1.363 (5)	C15—C16	1.406 (6)
O6—C12	1.219 (4)	C15—H15	0.9300
O2—C1	1.333 (5)	C16—C17	1.406 (5)
O2—H2	0.8200	C16—C21	1.431 (6)
O3—C3	1.392 (5)	C17—C18	1.426 (5)
O3—C2	1.422 (5)	C18—C19	1.411 (6)
O1—C1	1.201 (5)	C19—C22	1.405 (6)
O4—C10	1.252 (5)	C19—C20	1.437 (6)
C1—C2	1.510 (6)	C20—C21	1.331 (6)
C2—H2A	0.9700	C20—H20	0.9300
C2—H2B	0.9700	C21—H21	0.9300
C3—C4	1.376 (6)	C22—C23	1.354 (6)
C3—C8	1.382 (6)	C22—H22	0.9300
C4—C5	1.381 (6)	C23—C24	1.395 (6)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.393 (5)	C24—H24	0.9300

O7—Cu1—O5	92.08 (11)	C3—C8—C7	120.5 (4)
O7—Cu1—N2	171.29 (12)	C3—C8—H8	119.8
O5—Cu1—N2	93.61 (12)	C7—C8—H8	119.8
O7—Cu1—N3	91.96 (12)	N1—C9—C10	115.5 (3)
O5—Cu1—N3	170.40 (12)	N1—C9—H9A	108.4
N2—Cu1—N3	81.44 (13)	C10—C9—H9A	108.4
O7—Cu1—O7ⁱ	77.11 (11)	N1—C9—H9B	108.4
O5—Cu1—O7ⁱ	93.01 (10)	C10—C9—H9B	108.4
N2—Cu1—O7ⁱ	109.13 (11)	H9A—C9—H9B	107.5
N3—Cu1—O7ⁱ	96.38 (11)	O4—C10—O5	123.8 (4)
O7—Cu1—N1	74.69 (11)	O4—C10—C9	116.0 (4)
O5—Cu1—N1	76.84 (11)	O5—C10—C9	120.2 (3)
N2—Cu1—N1	100.21 (12)	N1—C11—C12	111.2 (3)
N3—Cu1—N1	95.87 (12)	N1—C11—H11A	109.4
O7ⁱ—Cu1—N1	149.54 (10)	C12—C11—H11A	109.4
C10—O5—Cu1	119.6 (2)	N1—C11—H11B	109.4
C12—O7—Cu1	120.4 (2)	C12—C11—H11B	109.4
C12—O7—Cu1ⁱ	134.3 (2)	H11A—C11—H11B	108.0
Cu1—O7—Cu1ⁱ	102.89 (11)	O6—C12—O7	124.5 (4)
C6—N1—C11	119.6 (3)	O6—C12—C11	119.4 (4)
C6—N1—C9	115.8 (3)	O7—C12—C11	116.1 (3)
C11—N1—C9	111.7 (3)	N3—C13—C14	122.9 (4)
C6—N1—Cu1	108.0 (2)	N3—C13—H13	118.5
C11—N1—Cu1	96.4 (2)	C14—C13—H13	118.5
C9—N1—Cu1	101.4 (2)	C15—C14—C13	119.0 (4)
C24—N2—C18	118.2 (4)	C15—C14—H14	120.5
C24—N2—Cu1	128.9 (3)	C13—C14—H14	120.5
C18—N2—Cu1	112.4 (3)	C14—C15—C16	120.3 (4)
C13—N3—C17	117.8 (3)	C14—C15—H15	119.9
C13—N3—Cu1	130.4 (3)	C16—C15—H15	119.9
C17—N3—Cu1	111.3 (3)	C17—C16—C15	116.6 (4)
C1—O2—H2	109.5	C17—C16—C21	117.8 (4)
C3—O3—C2	117.1 (4)	C15—C16—C21	125.5 (4)
O1—C1—O2	124.9 (4)	N3—C17—C16	123.2 (4)
O1—C1—C2	125.0 (4)	N3—C17—C18	116.1 (3)
O2—C1—C2	110.1 (4)	C16—C17—C18	120.7 (4)
O3—C2—C1	112.3 (4)	N2—C18—C19	123.1 (4)
O3—C2—H2A	109.1	N2—C18—C17	116.9 (4)
C1—C2—H2A	109.1	C19—C18—C17	120.0 (4)
O3—C2—H2B	109.1	C22—C19—C18	116.2 (4)
C1—C2—H2B	109.1	C22—C19—C20	126.3 (4)
H2A—C2—H2B	107.9	C18—C19—C20	117.6 (4)
C4—C3—C8	119.2 (4)	C21—C20—C19	122.1 (4)
C4—C3—O3	124.2 (4)	C21—C20—H20	118.9
C8—C3—O3	116.5 (4)	C19—C20—H20	118.9
C3—C4—C5	120.2 (4)	C20—C21—C16	121.7 (4)
C3—C4—H4	119.9	C20—C21—H21	119.1
C5—C4—H4	119.9	C16—C21—H21	119.1
C4—C5—C6	121.9 (4)	C23—C22—C19	120.3 (4)
C4—C5—H5	119.1	C23—C22—H22	119.8
C6—C5—H5	119.1	C19—C22—H22	119.8
C7—C6—C5	117.4 (4)	C22—C23—C24	120.1 (4)
C7—C6—N1	123.3 (3)	C22—C23—H23	119.9
C5—C6—N1	119.2 (3)	C24—C23—H23	119.9
C6—C7—C8	120.8 (4)	N2—C24—C23	122.1 (4)
C6—C7—H7	119.6	N2—C24—H24	119.0
C8—C7—H7	119.6	C23—C24—H24	119.0

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4ⁱⁱ	0.82	1.82	2.622 (4)	164

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

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₂H₁₁NO₇)₂(C₁₂H₈N₂)₂]
M_r	1049.92
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.7410 (17), 10.886 (2), 22.239 (4)
β (°)	90.85 (3)
V (Å³)	2115.8 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.09
Crystal size (mm)	0.26 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Mercury CCD area-detector
Absorption correction	Multi-scan (RAPID-AUTO; Rigaku, 1998)
T_min, T_max	0.85, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	14139, 3604, 3408
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.588

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.103, 1.25
No. of reflections	3604
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.35

Computer programs: CrystalClear (Rigaku, 2002), CrystalClear (Rigaku, 2002, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—O7	1.987 (3)	Cu1—N3	2.049 (3)
Cu1—O5	1.997 (3)	Cu1—O7ⁱ	2.293 (3)
Cu1—N2	2.003 (3)	Cu1—N1	2.460 (3)

O7—Cu1—O5	92.08 (11)	N2—Cu1—O7ⁱ	109.13 (11)
O7—Cu1—N2	171.29 (12)	N3—Cu1—O7ⁱ	96.38 (11)
O5—Cu1—N2	93.61 (12)	O7—Cu1—N1	74.69 (11)
O7—Cu1—N3	91.96 (12)	O5—Cu1—N1	76.84 (11)
O5—Cu1—N3	170.40 (12)	N2—Cu1—N1	100.21 (12)
N2—Cu1—N3	81.44 (13)	N3—Cu1—N1	95.87 (12)
O7—Cu1—O7ⁱ	77.11 (11)	O7ⁱ—Cu1—N1	149.54 (10)
O5—Cu1—O7ⁱ	93.01 (10)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4ⁱⁱ	0.82	1.82	2.622 (4)	163.9

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

References

Dong, Y. B., Xu, H. X., Ma, J. P. & Huang, R. O. (2006). Inorg. Chem. 45, 3325–3343. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ghermani, N.-E., Lecomte, C., Rapin, C., Steinmetz, P., Steinmetz, J. & Malaman, B. (1994). Acta Cryst. B50, 157–160. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Kido, T., Ikuta, Y., Sunatsuki, Y., Ogawa, Y. & Matsumoto, N. (2003). Inorg. Chem. 42, 398–408. Web of Science CSD CrossRef PubMed CAS Google Scholar
Pan, Z. R., Zheng, H. G., Wang, T. W., Song, Y., Li, Y. Z., Guo, Z. J. & Batten, S. R. (2008). Inorg. Chem. 47, 9528–9536. Web of Science CSD CrossRef PubMed CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2002). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Ruiz-Perez, C., Sanchiz, J., Molina, M. H., Lloret, F. & Julve, M. (2000). Inorg. Chem. 39, 1363–1370. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Volume 66| Part 12| December 2010| Pages m1670-m1671

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis(μ-2,2′-{[4-(carb­­oxy­meth­­oxy)phen­yl]aza­nedi­yl}di­acetato)­bis­­[(1,10-phenanthroline)copper(II)]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Bis(μ-2,2′-{[4-(carboxymethoxy)phenyl]azanediyl}diacetato)bis[(1,10-phenanthroline)copper(II)]