Bis(2-methyl­benzoato-κ2O,O′)(1,10′-phenanthroline-κ2N,N′)copper(II)

Ni, S.-L.; Zhou, F.; Qi, J.-L.

doi:10.1107/S1600536811018162

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page m779

doi:10.1107/S1600536811018162

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Bis(2-methylbenzoato-κ²O,O′)(1,10′-phenanthroline-κ²N,N′)copper(II)

Sheng-Liang Ni,^a ^* Feng Zhou ^a and Jin-Li Qi ^a

^aDepartment of Chemistry, Huzhou Teachers College, Huzhou, Zhejiang, 313000, People's Republic of China
^*Correspondence e-mail: shengliangni@163.com

(Received 10 May 2011; accepted 13 May 2011; online 20 May 2011)

In the title compound, [Cu(C₈H₇O₂)₂(C₁₂H₈N₂)], the Cu^II atom assumes a distorted octahedral coordination geometry, chelated by two N atoms from the 1,10′-phenanthroline ligand and four O atoms from two 2-methylbenzoate anions. A significant Jahn–Teller distortion is observed with two axial Cu—O distances significantly longer than those in the equatorial CuO₂N₂ plane. In the crystal, π–π stacking interactions, with centroid–centroid distances of 3.547 (3) or 3.728 (3) Å between the phenanthroline rings, form layers parallel to (011).

Related literature

For Jahn–Teller distortions in copper complexes, see: Yang & Vittal (2003 ); Su et al. (2005 ); Liu et al. (2010 ). For phenanthroline complexes, see: Wang et al. (1996 ); Wall et al. (1999 ); Naing et al. (1995 ). For related structures, see: Cano et al. (1997 ); Rodrigues et al. (1999 ) Xu & Xu (2004 ).

Experimental

Crystal data

[Cu(C₈H₇O₂)₂(C₁₂H₈N₂)]
M_r = 514.02
Monoclinic, P 2₁ /c
a = 16.245 (3) Å
b = 10.136 (2) Å
c = 14.048 (3) Å
β = 99.15 (3)°
V = 2283.7 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.00 mm⁻¹
T = 293 K
0.15 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.866, T_max = 0.900
17441 measured reflections
4021 independent reflections
2509 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.150
S = 1.13
4021 reflections
319 parameters
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −1.04 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu—O3	1.919 (4)
Cu—O1	1.927 (4)
Cu—N2	2.010 (4)
Cu—N1	2.025 (4)

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018162/sj5144sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018162/sj5144Isup2.hkl

checkCIF report

Comment top

The Jahn-Teller distortion of copper(II) complexes is well known. Most copper(II) complexes display an elongated distortion, and the coordinate bonds in the axial direction are usually longer than those in the equatorial coordination plane by 0.2–0.6 Å (Yang & Vittal, 2003; Su et al., 2005; Liu et al., 2010). Metal-phenanthroline complexes and their derivatives have also attracted much attention (Wang et al., 1996; Wall et al., 1999; Naing et al., 1995). In the title copper(II) phenanthroline complex, (I), a pair of long Cu-O bonds is observed.

The molecular structure of the title complex is shown in Fig. 1. The Cu^II ion binds to a phenanthroline molecule and two 2-methylbenzoate anions in a distorted octahedral geometry. Two N atoms from phen and two O atoms from carboxyl groups form a tetrahedrally distorted equatorial coordination plane, with a dihedral angle of 7.3 (2) ° between the Cu/O1/O3 and Cu/N1/N2 planes. The bond lengths in the equatorial plane are normal (Table 1). In the axial direction, the Cu-O distances (Cu-O2 2.609 (4) Å, Cu-O4 2.666 (4) Å) are longer than the Cu-O distances(Cu-O1 1.927 (4) Å, Cu-O3 1.919 (4) Å) equatorial plane.

The Cu-O-C angles of (Cu-O1-C13 105.9 (3) °, Cu-O3-C21 108.2 (3) °) are similar to values found in copper(II) complexes with a chelating benzoate ligand, for example, 106.1 (4) ° (Cano et al., 1997) and 104.5 (1) ° (Xu & Xu, 2004), but are much smaller than those in copper(II) complexes with a monodentate benzoate ligand, for example, 131.8 (1) ° (Rodrigues et al., 1999). This suggests the existence of a bonding interaction between atoms Cu and O2, Cu and O4. Besides the elongated Jahn-Teller distortion, the smaller O2-Cu-O4 angle of 132.1 (1) Å is also a possible reason for the larger differences within the same carboxylate group.

In the crystal structure two-dimensional layers form parallel to (011) through π–π packing interactions with centroid to centroid distances 3.547 (3) Å and 3.728 (3) Å between the phenanthroline rings, as shown in Fig. 2.

Related literature top

For Jahn–Teller distortions in copper complexes, see: Yang & Vittal (2003); Su et al. (2005); Liu et al. (2010). For phenanthroline complexes, see: Wang et al. (1996); Wall et al. (1999); Naing et al. (1995). For related structures, see: Cano et al. (1997); Rodrigues et al. (1999) Xu & Xu (2004).

Experimental top

Freshly prepared CuCO₃ was essential for an optimal synthesis. 1.0 cm³ (1 M) aqueous Na₂CO₃ was added dropwise to a stirred aqueous solution of (0.2490 g, 1.0 mmol)CuSO₄.5H₂O in 4 cm³ of doubly distilled water. This produced a blue precipitate, of Cu(OH)_2-2x(CO₃)_x.yH₂O, which was centrifuged and washed with doubly distilled water until no SO₄^-2 anions were detected in the supernatant liquid. The fresh blue precipitate was subsequently added to a stirred solution of 2-methylbenzoic acid (0.2725 g, 2.0 mmol) and 1,10'-phenanthroline (0.1982 g, 1.0 mmol) in 20 cm³ C₂H₅OH-H₂O (1:1, v/v). The mixture was stirred for 30 min and filtered. The insoluble solid was then filtered off, and the resulting blue filtrate (pH = 5.20) was allowed to stand at room temperature. Blue block-like crystals were grown by slow evaporation over a week. Yield: 45% based on the initial CuSO₄.5 H₂O.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound with dispalcement ellipsoids drawn at the 45% probability level.
	Fig. 2. Crystal packing showing the two-dimensional layer structure linked through π–π stacking interactions.

Bis(2-methylbenzoato-κ²O,O')(1,10'-phenanthroline- κ²N,N')copper(II) top

Crystal data top

[Cu(C₈H₇O₂)₂(C₁₂H₈N₂)]	F(000) = 1060
M_r = 514.02	D_x = 1.495 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 16.245 (3) Å	θ = 3.0–25.0°
b = 10.136 (2) Å	µ = 1.00 mm⁻¹
c = 14.048 (3) Å	T = 293 K
β = 99.15 (3)°	Plate, blue
V = 2283.7 (8) Å³	0.15 × 0.10 × 0.10 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4021 independent reflections
Radiation source: fine-focus sealed tube	2509 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −19→19
T_min = 0.866, T_max = 0.900	k = −12→12
17441 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.150	w = 1/[σ²(F_o²) + (0.0447P)² + 4.7675P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
4021 reflections	Δρ_max = 0.74 e Å⁻³
319 parameters	Δρ_min = −1.04 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0013 (5)

Crystal data top

[Cu(C₈H₇O₂)₂(C₁₂H₈N₂)]	V = 2283.7 (8) Å³
M_r = 514.02	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.245 (3) Å	µ = 1.00 mm⁻¹
b = 10.136 (2) Å	T = 293 K
c = 14.048 (3) Å	0.15 × 0.10 × 0.10 mm
β = 99.15 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4021 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2509 reflections with I > 2σ(I)
T_min = 0.866, T_max = 0.900	R_int = 0.063
17441 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.13	Δρ_max = 0.74 e Å⁻³
4021 reflections	Δρ_min = −1.04 e Å⁻³
319 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
Cu	−0.33221 (4)	0.96309 (7)	−0.17022 (4)	0.0480 (2)
O1	−0.2996 (2)	1.1433 (4)	−0.1871 (3)	0.0703 (12)
O2	−0.2404 (2)	1.1033 (4)	−0.0382 (3)	0.0606 (10)
O3	−0.2325 (2)	0.8925 (4)	−0.2077 (3)	0.0635 (11)
O4	−0.3140 (2)	0.8977 (4)	−0.3495 (3)	0.0609 (10)
N1	−0.3735 (2)	0.7809 (4)	−0.1419 (3)	0.0450 (10)
N2	−0.4462 (2)	1.0137 (4)	−0.1442 (3)	0.0423 (9)
C1	−0.3348 (4)	0.6641 (6)	−0.1404 (4)	0.0584 (15)
H1	−0.2794	0.6613	−0.1496	0.070*
C2	−0.3756 (5)	0.5461 (6)	−0.1255 (4)	0.0698 (17)
H2	−0.3471	0.4665	−0.1251	0.084*
C3	−0.4558 (4)	0.5468 (6)	−0.1115 (4)	0.0607 (15)
H3	−0.4825	0.4678	−0.1024	0.073*
C4	−0.4990 (3)	0.6670 (5)	−0.1108 (3)	0.0478 (13)
C5	−0.5834 (3)	0.6805 (6)	−0.0943 (4)	0.0587 (15)
H5	−0.6141	0.6053	−0.0854	0.070*
C6	−0.6191 (3)	0.7998 (7)	−0.0914 (4)	0.0588 (15)
H6	−0.6734	0.8055	−0.0785	0.071*
C7	−0.5753 (3)	0.9185 (6)	−0.1076 (3)	0.0482 (13)
C8	−0.6084 (4)	1.0457 (6)	−0.1077 (4)	0.0606 (16)
H8	−0.6627	1.0579	−0.0962	0.073*
C9	−0.5615 (4)	1.1519 (6)	−0.1244 (4)	0.0623 (16)
H9	−0.5833	1.2366	−0.1235	0.075*
C10	−0.4806 (4)	1.1328 (5)	−0.1431 (4)	0.0565 (14)
H10	−0.4494	1.2061	−0.1552	0.068*
C11	−0.4933 (3)	0.9076 (5)	−0.1268 (3)	0.0395 (11)
C12	−0.4540 (3)	0.7812 (5)	−0.1262 (3)	0.0406 (11)
C13	−0.2490 (3)	1.1732 (5)	−0.1108 (4)	0.0476 (12)
C14	−0.2009 (3)	1.3008 (5)	−0.1152 (3)	0.0416 (11)
C15	−0.2043 (3)	1.3578 (5)	−0.2067 (4)	0.0509 (13)
H15	−0.2348	1.3161	−0.2599	0.061*
C16	−0.1637 (3)	1.4737 (6)	−0.2196 (4)	0.0619 (15)
H16	−0.1660	1.5092	−0.2811	0.074*
C17	−0.1197 (4)	1.5370 (6)	−0.1411 (5)	0.0667 (16)
H17	−0.0928	1.6163	−0.1490	0.080*
C18	−0.1157 (3)	1.4830 (6)	−0.0517 (5)	0.0604 (15)
H18	−0.0859	1.5272	0.0008	0.072*
C19	−0.1545 (3)	1.3636 (5)	−0.0356 (4)	0.0496 (13)
C20	−0.1458 (4)	1.3130 (7)	0.0666 (4)	0.080 (2)
H20A	−0.1327	1.2206	0.0676	0.120*
H20B	−0.1973	1.3262	0.0907	0.120*
H20C	−0.1019	1.3600	0.1063	0.120*
C21	−0.2458 (3)	0.8741 (5)	−0.2988 (4)	0.0494 (13)
C22	−0.1747 (3)	0.8162 (5)	−0.3429 (3)	0.0425 (11)
C23	−0.1959 (3)	0.7396 (5)	−0.4251 (3)	0.0531 (14)
H23	−0.2517	0.7325	−0.4527	0.064*
C24	−0.1363 (4)	0.6736 (6)	−0.4669 (4)	0.0615 (15)
H24	−0.1517	0.6217	−0.5214	0.074*
C25	−0.0538 (4)	0.6861 (6)	−0.4265 (4)	0.0612 (15)
H25	−0.0130	0.6410	−0.4528	0.073*
C26	−0.0319 (3)	0.7651 (6)	−0.3470 (4)	0.0555 (14)
H26	0.0243	0.7750	−0.3220	0.067*
C27	−0.0903 (3)	0.8306 (5)	−0.3028 (3)	0.0430 (12)
C28	−0.0598 (3)	0.9171 (6)	−0.2164 (4)	0.0629 (16)
H18A	−0.0909	0.9981	−0.2215	0.094*
H28B	−0.0017	0.9361	−0.2144	0.094*
H28C	−0.0676	0.8720	−0.1584	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.0409 (4)	0.0540 (4)	0.0480 (4)	−0.0059 (3)	0.0037 (3)	0.0006 (3)
O1	0.067 (2)	0.074 (3)	0.063 (2)	−0.024 (2)	−0.011 (2)	0.009 (2)
O2	0.075 (3)	0.049 (2)	0.057 (2)	−0.006 (2)	0.0108 (19)	0.0059 (19)
O3	0.049 (2)	0.094 (3)	0.048 (2)	−0.005 (2)	0.0121 (17)	0.000 (2)
O4	0.045 (2)	0.060 (2)	0.074 (3)	−0.0035 (18)	−0.0034 (18)	0.005 (2)
N1	0.040 (2)	0.053 (3)	0.041 (2)	0.010 (2)	0.0046 (17)	−0.003 (2)
N2	0.051 (2)	0.035 (2)	0.039 (2)	0.0028 (19)	0.0003 (18)	0.0003 (18)
C1	0.059 (3)	0.059 (4)	0.056 (3)	0.022 (3)	0.005 (3)	−0.002 (3)
C2	0.105 (5)	0.041 (3)	0.065 (4)	0.018 (4)	0.019 (4)	0.004 (3)
C3	0.091 (5)	0.044 (3)	0.050 (3)	−0.007 (3)	0.019 (3)	−0.001 (3)
C4	0.056 (3)	0.047 (3)	0.039 (3)	−0.009 (3)	0.001 (2)	−0.003 (2)
C5	0.054 (3)	0.075 (4)	0.047 (3)	−0.027 (3)	0.005 (3)	−0.001 (3)
C6	0.041 (3)	0.084 (5)	0.050 (3)	−0.007 (3)	0.004 (2)	−0.007 (3)
C7	0.040 (3)	0.062 (4)	0.039 (3)	0.006 (3)	−0.002 (2)	−0.005 (2)
C8	0.050 (3)	0.078 (4)	0.050 (3)	0.025 (3)	−0.002 (2)	−0.009 (3)
C9	0.070 (4)	0.059 (4)	0.053 (3)	0.031 (3)	−0.004 (3)	−0.009 (3)
C10	0.081 (4)	0.040 (3)	0.044 (3)	0.006 (3)	−0.004 (3)	0.003 (2)
C11	0.039 (3)	0.044 (3)	0.033 (2)	0.002 (2)	−0.003 (2)	−0.002 (2)
C12	0.041 (3)	0.042 (3)	0.035 (2)	0.005 (2)	−0.003 (2)	−0.005 (2)
C13	0.041 (3)	0.042 (3)	0.061 (3)	0.001 (2)	0.013 (3)	0.000 (3)
C14	0.036 (2)	0.039 (3)	0.050 (3)	0.000 (2)	0.007 (2)	−0.001 (2)
C15	0.043 (3)	0.054 (3)	0.056 (3)	−0.003 (2)	0.006 (2)	0.005 (3)
C16	0.057 (3)	0.061 (4)	0.071 (4)	0.003 (3)	0.021 (3)	0.021 (3)
C17	0.060 (4)	0.047 (3)	0.096 (5)	−0.006 (3)	0.023 (3)	0.000 (4)
C18	0.049 (3)	0.053 (4)	0.079 (4)	−0.007 (3)	0.008 (3)	−0.018 (3)
C19	0.046 (3)	0.053 (3)	0.051 (3)	−0.005 (3)	0.011 (2)	−0.006 (3)
C20	0.086 (5)	0.098 (5)	0.053 (4)	−0.023 (4)	0.002 (3)	−0.003 (3)
C21	0.039 (3)	0.053 (3)	0.057 (3)	−0.013 (2)	0.007 (2)	0.006 (3)
C22	0.044 (3)	0.042 (3)	0.043 (3)	−0.005 (2)	0.009 (2)	0.007 (2)
C23	0.058 (3)	0.056 (3)	0.043 (3)	−0.015 (3)	0.002 (2)	0.003 (3)
C24	0.088 (4)	0.050 (3)	0.049 (3)	−0.014 (3)	0.017 (3)	−0.007 (3)
C25	0.070 (4)	0.054 (4)	0.063 (4)	0.006 (3)	0.022 (3)	0.000 (3)
C26	0.051 (3)	0.062 (4)	0.053 (3)	−0.001 (3)	0.007 (3)	0.002 (3)
C27	0.042 (3)	0.041 (3)	0.045 (3)	−0.002 (2)	0.007 (2)	0.005 (2)
C28	0.048 (3)	0.079 (4)	0.061 (3)	−0.014 (3)	0.003 (3)	−0.013 (3)

Geometric parameters (Å, º) top

Cu—O3	1.919 (4)	C11—C12	1.431 (6)
Cu—O1	1.927 (4)	C13—C14	1.518 (7)
Cu—N2	2.010 (4)	C14—C19	1.399 (7)
Cu—N1	2.025 (4)	C14—C15	1.402 (7)
O1—C13	1.279 (6)	C15—C16	1.374 (7)
O2—C13	1.230 (6)	C15—H15	0.9300
O3—C21	1.277 (6)	C16—C17	1.374 (8)
O4—C21	1.240 (6)	C16—H16	0.9300
N1—C1	1.339 (6)	C17—C18	1.362 (8)
N1—C12	1.361 (6)	C17—H17	0.9300
N2—C10	1.332 (6)	C18—C19	1.399 (7)
N2—C11	1.364 (6)	C18—H18	0.9300
C1—C2	1.399 (8)	C19—C20	1.510 (7)
C1—H1	0.9300	C20—H20A	0.9600
C2—C3	1.348 (8)	C20—H20B	0.9600
C2—H2	0.9300	C20—H20C	0.9600
C3—C4	1.406 (7)	C21—C22	1.515 (7)
C3—H3	0.9300	C22—C23	1.388 (7)
C4—C12	1.404 (7)	C22—C27	1.404 (6)
C4—C5	1.434 (7)	C23—C24	1.382 (8)
C5—C6	1.345 (8)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.375 (8)
C6—C7	1.435 (8)	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.374 (7)
C7—C8	1.398 (7)	C25—H25	0.9300
C7—C11	1.404 (7)	C26—C27	1.383 (7)
C8—C9	1.360 (8)	C26—H26	0.9300
C8—H8	0.9300	C27—C28	1.516 (7)
C9—C10	1.393 (8)	C28—H18A	0.9600
C9—H9	0.9300	C28—H28B	0.9600
C10—H10	0.9300	C28—H28C	0.9600

O3—Cu—O1	93.39 (18)	O1—C13—C14	115.7 (5)
O3—Cu—N2	170.71 (16)	C19—C14—C15	118.9 (5)
O1—Cu—N2	93.45 (17)	C19—C14—C13	124.8 (4)
O3—Cu—N1	91.94 (17)	C15—C14—C13	116.3 (4)
O1—Cu—N1	173.96 (17)	C16—C15—C14	121.6 (5)
N2—Cu—N1	81.58 (15)	C16—C15—H15	119.2
C13—O1—Cu	105.9 (3)	C14—C15—H15	119.2
C21—O3—Cu	108.2 (3)	C15—C16—C17	119.5 (5)
C1—N1—C12	117.4 (5)	C15—C16—H16	120.3
C1—N1—Cu	129.8 (4)	C17—C16—H16	120.3
C12—N1—Cu	112.7 (3)	C18—C17—C16	119.7 (6)
C10—N2—C11	117.7 (4)	C18—C17—H17	120.2
C10—N2—Cu	129.3 (4)	C16—C17—H17	120.2
C11—N2—Cu	113.0 (3)	C17—C18—C19	122.7 (5)
N1—C1—C2	121.7 (5)	C17—C18—H18	118.7
N1—C1—H1	119.1	C19—C18—H18	118.7
C2—C1—H1	119.1	C14—C19—C18	117.6 (5)
C3—C2—C1	120.6 (6)	C14—C19—C20	124.2 (5)
C3—C2—H2	119.7	C18—C19—C20	118.1 (5)
C1—C2—H2	119.7	C19—C20—H20A	109.5
C2—C3—C4	120.0 (5)	C19—C20—H20B	109.5
C2—C3—H3	120.0	H20A—C20—H20B	109.5
C4—C3—H3	120.0	C19—C20—H20C	109.5
C12—C4—C3	116.2 (5)	H20A—C20—H20C	109.5
C12—C4—C5	118.7 (5)	H20B—C20—H20C	109.5
C3—C4—C5	125.1 (5)	O4—C21—O3	122.7 (5)
C6—C5—C4	121.3 (5)	O4—C21—C22	120.6 (5)
C6—C5—H5	119.4	O3—C21—C22	116.6 (4)
C4—C5—H5	119.4	C23—C22—C27	119.3 (5)
C5—C6—C7	121.4 (5)	C23—C22—C21	116.9 (4)
C5—C6—H6	119.3	C27—C22—C21	123.7 (4)
C7—C6—H6	119.3	C24—C23—C22	121.7 (5)
C8—C7—C11	116.7 (5)	C24—C23—H23	119.2
C8—C7—C6	124.9 (5)	C22—C23—H23	119.2
C11—C7—C6	118.4 (5)	C25—C24—C23	118.8 (5)
C9—C8—C7	120.3 (5)	C25—C24—H24	120.6
C9—C8—H8	119.9	C23—C24—H24	120.6
C7—C8—H8	119.9	C26—C25—C24	119.9 (5)
C8—C9—C10	119.6 (5)	C26—C25—H25	120.0
C8—C9—H9	120.2	C24—C25—H25	120.0
C10—C9—H9	120.2	C25—C26—C27	122.4 (5)
N2—C10—C9	122.5 (5)	C25—C26—H26	118.8
N2—C10—H10	118.7	C27—C26—H26	118.8
C9—C10—H10	118.7	C26—C27—C22	117.7 (5)
N2—C11—C7	123.2 (5)	C26—C27—C28	118.5 (4)
N2—C11—C12	116.4 (4)	C22—C27—C28	123.7 (4)
C7—C11—C12	120.3 (5)	C27—C28—H18A	109.5
N1—C12—C4	124.1 (4)	C27—C28—H28B	109.5
N1—C12—C11	116.1 (4)	H18A—C28—H28B	109.5
C4—C12—C11	119.8 (4)	C27—C28—H28C	109.5
O2—C13—O1	122.1 (5)	H18A—C28—H28C	109.5
O2—C13—C14	122.2 (5)	H28B—C28—H28C	109.5

Experimental details

Crystal data
Chemical formula	[Cu(C₈H₇O₂)₂(C₁₂H₈N₂)]
M_r	514.02
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	16.245 (3), 10.136 (2), 14.048 (3)
β (°)	99.15 (3)
V (Å³)	2283.7 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.00
Crystal size (mm)	0.15 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.866, 0.900
No. of measured, independent and observed [I > 2σ(I)] reflections	17441, 4021, 2509
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.150, 1.13
No. of reflections	4021
No. of parameters	319
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.74, −1.04

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu—O3	1.919 (4)	Cu—N2	2.010 (4)
Cu—O1	1.927 (4)	Cu—N1	2.025 (4)

Acknowledgements

This project was supported by the Foundation of the Education Department of Zhejiang Province (ZC200805662).

References

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