Bis[2-(cyclo­pentyl­imino­meth­yl)-5-meth­oxy­phenolato]copper(II)

Ji, X.-H.; Lu, J.-F.

doi:10.1107/S1600536810025481

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m881

https://doi.org/10.1107/S1600536810025481

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Bis[2-(cyclopentyliminomethyl)-5-methoxyphenolato]copper(II)

Xiao-Hui Ji ^a and Jiu-Fu Lu ^a ^*

^aSchool of Chemistry and Environmental Science, Shaanxi University of Technology, Hanzhong 723000, People's Republic of China
^*Correspondence e-mail: jiufulu@163.com

(Received 26 June 2010; accepted 29 June 2010; online 3 July 2010)

The title compound, [Cu(C₁₃H₁₆NO₂)₂], is a mononuclear copper(II) complex derived from the Schiff base ligand 2-(cyclopentyliminomethyl)-5-methoxyphenol and copper acetate. The Cu^II atom is four-coordinated by the phenolate O atoms and imine N atoms from two Schiff base ligands, in a highly distorted square-planar geometry. The O- and N-donor atoms are mutually trans and the dihedral angle between the two benzene rings is 55.8 (3)°.

Related literature

For background to complexes with Schiff bases, see: Hamaker et al. (2010 ); Wang et al. (2010 ); Mirkhani et al. (2010 ); Liu & Yang (2009 ); Keypour et al. (2009 ); Adhikary et al. (2009 ); Peng et al. (2009 ). For similar copper complexes, see: Friščić et al. (2002 ); Marsh & Spek (2001 ); Han et al. (2001 ); Akitsu & Einaga (2004 ); Dhar et al. (2003 ).

Experimental

Crystal data

[Cu(C₁₃H₁₆NO₂)₂]
M_r = 500.08
Monoclinic, P 2₁ /n
a = 8.496 (1) Å
b = 14.054 (2) Å
c = 20.442 (2) Å
β = 100.236 (3)°
V = 2402.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 298 K
0.23 × 0.21 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.812, T_max = 0.826
12222 measured reflections
4333 independent reflections
3131 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.163
S = 1.00
4333 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −1.16 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—O1	1.890 (2)
Cu1—O3	1.891 (2)
Cu1—N2	1.967 (3)
Cu1—N1	1.978 (3)

O1—Cu1—O3	144.60 (13)
O1—Cu1—N2	93.93 (11)
O3—Cu1—N2	95.32 (11)
O1—Cu1—N1	95.40 (11)
O3—Cu1—N1	94.20 (11)
N2—Cu1—N1	148.66 (12)

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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: https://doi.org/10.1107/S1600536810025481/sj5030sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025481/sj5030Isup2.hkl

checkCIF report

Comment top

Schiff bases are known to be versatile ligands in coordination chemistry (Hamaker et al., 2010; Wang et al., 2010; Mirkhani et al., 2010; Liu & Yang, 2009). A large number of complexes with Schiff bases have been reported because of their interesting structures and potential applications (Keypour et al., 2009; Adhikary et al., 2009; Peng et al., 2009). We report here the crystal structure of the title new copper complex with the Schiff base ligand 2-(cyclopentyliminomethyl)-5-methoxyphenol.

The Cu atom in the complex is four-coordinated by two phenolate O atoms and two imine N atoms from two Schiff base ligands, forming a distorted square planar geometry (Fig. 1). The dihedral angle between the C1-C6 and C14-C19 benzene rings is 55.8 (3)°. The bond lengths (Table 1) involving the Cu atom are comparable to those observed in similar copper complexes (Friščić et al., 2002; Marsh & Spek, 2001; Han et al., 2001; Akitsu & Einaga, 2004; Dhar et al., 2003).

Related literature top

For background to complexes with Schiff bases, see: Hamaker et al. (2010); Wang et al. (2010); Mirkhani et al. (2010); Liu & Yang (2009); Keypour et al. (2009); Adhikary et al. (2009); Peng et al. (2009). For similar copper complexes, see: Friščić et al. (2002); Marsh & Spek (2001); Han et al. (2001); Akitsu & Einaga, 2004; Dhar et al. (2003).

Experimental top

4-Methoxysalicylaldehyde (0.1 mmol, 15.2 mg) and cyclopentylamine (0.1 mmol, 8.5 mg) were mixed and stirred in methanol (10 ml) for 30 min. Then a methanol solution (5 ml) of copper acetate (0.1 mmol, 19.9 mg) was added to the mixture. The final mixture was stirred for another 30 min to give a blue solution. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of the solution at room temperature.

Structure description top

For background to complexes with Schiff bases, see: Hamaker et al. (2010); Wang et al. (2010); Mirkhani et al. (2010); Liu & Yang (2009); Keypour et al. (2009); Adhikary et al. (2009); Peng et al. (2009). For similar copper complexes, see: Friščić et al. (2002); Marsh & Spek (2001); Han et al. (2001); Akitsu & Einaga, 2004; Dhar et al. (2003).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Bis[2-(cyclopentyliminomethyl)-5-methoxyphenolato]copper(II) top

Crystal data top

[Cu(C₁₃H₁₆NO₂)₂]	F(000) = 1052
M_r = 500.08	D_x = 1.383 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3695 reflections
a = 8.496 (1) Å	θ = 2.5–25.1°
b = 14.054 (2) Å	µ = 0.94 mm⁻¹
c = 20.442 (2) Å	T = 298 K
β = 100.236 (3)°	Block, blue
V = 2402.0 (5) Å³	0.23 × 0.21 × 0.21 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4333 independent reflections
Radiation source: fine-focus sealed tube	3131 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
ω scans	θ_max = 25.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→10
T_min = 0.812, T_max = 0.826	k = −16→16
12222 measured reflections	l = −24→17

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0973P)²] where P = (F_o² + 2F_c²)/3
4333 reflections	(Δ/σ)_max = 0.001
300 parameters	Δρ_max = 0.69 e Å⁻³
0 restraints	Δρ_min = −1.16 e Å⁻³

Crystal data top

[Cu(C₁₃H₁₆NO₂)₂]	V = 2402.0 (5) Å³
M_r = 500.08	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.496 (1) Å	µ = 0.94 mm⁻¹
b = 14.054 (2) Å	T = 298 K
c = 20.442 (2) Å	0.23 × 0.21 × 0.21 mm
β = 100.236 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4333 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3131 reflections with I > 2σ(I)
T_min = 0.812, T_max = 0.826	R_int = 0.081
12222 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.00	Δρ_max = 0.69 e Å⁻³
4333 reflections	Δρ_min = −1.16 e Å⁻³
300 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
Cu1	−0.00311 (5)	0.84349 (3)	0.75910 (2)	0.0392 (2)
N1	−0.0266 (3)	0.8673 (2)	0.85224 (14)	0.0387 (7)
N2	0.0215 (3)	0.8950 (2)	0.67202 (13)	0.0367 (7)
O1	0.2109 (3)	0.80068 (19)	0.77995 (11)	0.0460 (6)
O2	0.6781 (3)	0.6732 (2)	0.91142 (15)	0.0597 (8)
O3	−0.2181 (3)	0.8050 (2)	0.73199 (11)	0.0487 (7)
O4	−0.6953 (3)	0.7268 (2)	0.58341 (13)	0.0608 (8)
C1	0.2376 (4)	0.8058 (3)	0.89943 (16)	0.0387 (8)
C2	0.2940 (4)	0.7847 (2)	0.83963 (16)	0.0376 (8)
C3	0.4436 (4)	0.7414 (2)	0.84350 (17)	0.0408 (8)
H3	0.4817	0.7276	0.8047	0.049*
C4	0.5355 (4)	0.7190 (3)	0.90438 (18)	0.0438 (9)
C5	0.4826 (5)	0.7423 (3)	0.96339 (18)	0.0510 (10)
H5	0.5457	0.7289	1.0044	0.061*
C6	0.3390 (4)	0.7843 (3)	0.96003 (18)	0.0481 (10)
H6	0.3051	0.7999	0.9995	0.058*
C7	0.7322 (5)	0.6397 (3)	0.8541 (2)	0.0614 (12)
H7A	0.6525	0.5990	0.8293	0.092*
H7B	0.8297	0.6046	0.8671	0.092*
H7C	0.7513	0.6928	0.8270	0.092*
C8	0.0844 (4)	0.8467 (2)	0.90186 (18)	0.0404 (9)
H8	0.0625	0.8599	0.9439	0.049*
C9	−0.1767 (4)	0.9093 (3)	0.86370 (17)	0.0414 (8)
H9	−0.2630	0.8665	0.8436	0.050*
C10	−0.2091 (5)	1.0059 (3)	0.8299 (2)	0.0653 (12)
H10A	−0.1117	1.0433	0.8349	0.078*
H10B	−0.2508	0.9980	0.7828	0.078*
C11	−0.3317 (6)	1.0539 (4)	0.8645 (3)	0.0819 (16)
H11A	−0.2954	1.1169	0.8796	0.098*
H11B	−0.4332	1.0599	0.8344	0.098*
C12	−0.3499 (5)	0.9915 (3)	0.9232 (2)	0.0670 (13)
H12A	−0.4458	0.9529	0.9131	0.080*
H12B	−0.3555	1.0298	0.9622	0.080*
C13	−0.2011 (5)	0.9294 (3)	0.9345 (2)	0.0563 (11)
H13A	−0.2186	0.8711	0.9575	0.068*
H13B	−0.1102	0.9629	0.9596	0.068*
C14	−0.2496 (4)	0.8557 (2)	0.61796 (17)	0.0393 (9)
C15	−0.3019 (4)	0.8089 (3)	0.67175 (17)	0.0390 (8)
C16	−0.4528 (4)	0.7646 (3)	0.66019 (17)	0.0432 (9)
H16	−0.4880	0.7324	0.6947	0.052*
C17	−0.5492 (4)	0.7683 (3)	0.59848 (18)	0.0448 (9)
C18	−0.4993 (5)	0.8175 (3)	0.54602 (19)	0.0540 (11)
H18	−0.5656	0.8213	0.5047	0.065*
C19	−0.3540 (4)	0.8592 (3)	0.55627 (18)	0.0497 (10)
H19	−0.3216	0.8916	0.5213	0.060*
C20	−0.7465 (6)	0.6658 (3)	0.6315 (3)	0.0699 (14)
H20A	−0.6642	0.6202	0.6469	0.105*
H20B	−0.8423	0.6332	0.6115	0.105*
H20C	−0.7675	0.7032	0.6683	0.105*
C21	−0.0928 (4)	0.8941 (2)	0.62103 (17)	0.0400 (8)
H21	−0.0707	0.9215	0.5822	0.048*
C22	0.1781 (4)	0.9340 (2)	0.66504 (17)	0.0386 (8)
H22	0.2540	0.8808	0.6702	0.046*
C23	0.1945 (4)	0.9857 (3)	0.60076 (18)	0.0472 (9)
H23A	0.1985	0.9408	0.5651	0.057*
H23B	0.1057	1.0290	0.5873	0.057*
C24	0.3521 (5)	1.0401 (3)	0.6185 (2)	0.0557 (11)
H24A	0.3421	1.1032	0.5989	0.067*
H24B	0.4372	1.0065	0.6022	0.067*
C25	0.3882 (5)	1.0467 (3)	0.6946 (2)	0.0631 (12)
H25A	0.4823	1.0096	0.7124	0.076*
H25B	0.4067	1.1123	0.7087	0.076*
C26	0.2415 (5)	1.0072 (3)	0.71846 (19)	0.0493 (10)
H26A	0.1632	1.0567	0.7208	0.059*
H26B	0.2703	0.9774	0.7617	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0408 (3)	0.0561 (3)	0.0189 (3)	0.00078 (18)	0.00073 (19)	0.00373 (18)
N1	0.0382 (17)	0.0517 (17)	0.0256 (16)	−0.0011 (13)	0.0040 (13)	0.0007 (13)
N2	0.0390 (16)	0.0482 (17)	0.0227 (15)	0.0050 (13)	0.0045 (12)	0.0025 (13)
O1	0.0477 (15)	0.0664 (16)	0.0218 (13)	0.0132 (13)	0.0001 (11)	0.0091 (12)
O2	0.0506 (17)	0.082 (2)	0.0432 (17)	0.0161 (14)	−0.0017 (14)	0.0044 (15)
O3	0.0483 (15)	0.0762 (17)	0.0189 (13)	−0.0110 (13)	−0.0013 (11)	0.0067 (12)
O4	0.0481 (17)	0.093 (2)	0.0370 (16)	−0.0184 (15)	−0.0033 (13)	−0.0022 (15)
C1	0.044 (2)	0.049 (2)	0.0206 (18)	0.0027 (16)	−0.0030 (15)	−0.0013 (16)
C2	0.047 (2)	0.0435 (19)	0.0215 (17)	−0.0014 (16)	0.0030 (15)	0.0049 (15)
C3	0.045 (2)	0.052 (2)	0.0262 (18)	0.0029 (17)	0.0067 (16)	0.0036 (16)
C4	0.042 (2)	0.050 (2)	0.036 (2)	0.0022 (16)	−0.0022 (16)	0.0066 (17)
C5	0.051 (2)	0.070 (3)	0.027 (2)	0.0025 (19)	−0.0074 (17)	0.0035 (19)
C6	0.055 (2)	0.067 (3)	0.0202 (18)	0.0014 (19)	0.0018 (17)	−0.0019 (18)
C7	0.053 (3)	0.071 (3)	0.061 (3)	0.019 (2)	0.012 (2)	0.009 (2)
C8	0.044 (2)	0.055 (2)	0.0227 (18)	−0.0036 (16)	0.0081 (16)	−0.0031 (16)
C9	0.040 (2)	0.055 (2)	0.0281 (19)	−0.0057 (16)	0.0050 (15)	−0.0045 (17)
C10	0.062 (3)	0.073 (3)	0.064 (3)	0.018 (2)	0.021 (2)	0.018 (2)
C11	0.092 (4)	0.082 (3)	0.076 (4)	0.032 (3)	0.028 (3)	0.010 (3)
C12	0.070 (3)	0.073 (3)	0.063 (3)	0.009 (2)	0.024 (2)	−0.017 (2)
C13	0.061 (3)	0.072 (3)	0.038 (2)	0.005 (2)	0.017 (2)	−0.005 (2)
C14	0.042 (2)	0.056 (2)	0.0185 (18)	0.0033 (16)	0.0012 (15)	0.0013 (15)
C15	0.043 (2)	0.051 (2)	0.0215 (18)	0.0045 (16)	0.0028 (15)	−0.0023 (16)
C16	0.044 (2)	0.061 (2)	0.0234 (18)	−0.0042 (17)	0.0024 (16)	0.0031 (17)
C17	0.044 (2)	0.060 (2)	0.0279 (19)	−0.0007 (17)	0.0004 (16)	−0.0064 (18)
C18	0.049 (2)	0.086 (3)	0.023 (2)	−0.002 (2)	−0.0044 (17)	0.001 (2)
C19	0.048 (2)	0.077 (3)	0.023 (2)	−0.0010 (19)	0.0031 (17)	0.0059 (18)
C20	0.061 (3)	0.087 (3)	0.060 (3)	−0.026 (2)	0.005 (2)	0.003 (3)
C21	0.044 (2)	0.054 (2)	0.0228 (18)	0.0017 (17)	0.0071 (15)	0.0070 (16)
C22	0.038 (2)	0.045 (2)	0.0319 (19)	0.0040 (15)	0.0053 (15)	0.0026 (16)
C23	0.053 (2)	0.056 (2)	0.034 (2)	−0.0034 (18)	0.0110 (18)	0.0057 (18)
C24	0.059 (3)	0.058 (2)	0.053 (3)	−0.013 (2)	0.020 (2)	−0.002 (2)
C25	0.065 (3)	0.068 (3)	0.053 (3)	−0.018 (2)	0.000 (2)	0.005 (2)
C26	0.057 (2)	0.056 (2)	0.034 (2)	−0.0040 (18)	0.0031 (18)	−0.0020 (18)

Geometric parameters (Å, º) top

Cu1—O1	1.890 (2)	C11—H11A	0.9700
Cu1—O3	1.891 (2)	C11—H11B	0.9700
Cu1—N2	1.967 (3)	C12—C13	1.520 (6)
Cu1—N1	1.978 (3)	C12—H12A	0.9700
N1—C8	1.289 (4)	C12—H12B	0.9700
N1—C9	1.462 (4)	C13—H13A	0.9700
N2—C21	1.292 (4)	C13—H13B	0.9700
N2—C22	1.469 (4)	C14—C19	1.408 (5)
O1—C2	1.316 (4)	C14—C15	1.419 (5)
O2—C4	1.356 (4)	C14—C21	1.428 (5)
O2—C7	1.414 (5)	C15—C16	1.407 (5)
O3—C15	1.309 (4)	C16—C17	1.378 (5)
O4—C17	1.356 (4)	C16—H16	0.9300
O4—C20	1.429 (5)	C17—C18	1.403 (5)
C1—C6	1.410 (5)	C18—C19	1.349 (5)
C1—C2	1.421 (5)	C18—H18	0.9300
C1—C8	1.432 (5)	C19—H19	0.9300
C2—C3	1.398 (5)	C20—H20A	0.9600
C3—C4	1.383 (5)	C20—H20B	0.9600
C3—H3	0.9300	C20—H20C	0.9600
C4—C5	1.399 (5)	C21—H21	0.9300
C5—C6	1.346 (5)	C22—C26	1.527 (5)
C5—H5	0.9300	C22—C23	1.529 (5)
C6—H6	0.9300	C22—H22	0.9800
C7—H7A	0.9600	C23—C24	1.529 (5)
C7—H7B	0.9600	C23—H23A	0.9700
C7—H7C	0.9600	C23—H23B	0.9700
C8—H8	0.9300	C24—C25	1.535 (6)
C9—C13	1.524 (5)	C24—H24A	0.9700
C9—C10	1.527 (5)	C24—H24B	0.9700
C9—H9	0.9800	C25—C26	1.522 (5)
C10—C11	1.518 (6)	C25—H25A	0.9700
C10—H10A	0.9700	C25—H25B	0.9700
C10—H10B	0.9700	C26—H26A	0.9700
C11—C12	1.516 (6)	C26—H26B	0.9700

O1—Cu1—O3	144.60 (13)	C13—C12—H12B	110.8
O1—Cu1—N2	93.93 (11)	H12A—C12—H12B	108.9
O3—Cu1—N2	95.32 (11)	C12—C13—C9	102.3 (3)
O1—Cu1—N1	95.40 (11)	C12—C13—H13A	111.3
O3—Cu1—N1	94.20 (11)	C9—C13—H13A	111.3
N2—Cu1—N1	148.66 (12)	C12—C13—H13B	111.3
C8—N1—C9	120.1 (3)	C9—C13—H13B	111.3
C8—N1—Cu1	122.4 (2)	H13A—C13—H13B	109.2
C9—N1—Cu1	117.6 (2)	C19—C14—C15	118.5 (3)
C21—N2—C22	119.3 (3)	C19—C14—C21	117.4 (3)
C21—N2—Cu1	122.7 (2)	C15—C14—C21	124.0 (3)
C22—N2—Cu1	118.0 (2)	O3—C15—C16	117.8 (3)
C2—O1—Cu1	126.8 (2)	O3—C15—C14	123.7 (3)
C4—O2—C7	119.1 (3)	C16—C15—C14	118.5 (3)
C15—O3—Cu1	126.8 (2)	C17—C16—C15	120.8 (3)
C17—O4—C20	118.7 (3)	C17—C16—H16	119.6
C6—C1—C2	117.6 (3)	C15—C16—H16	119.6
C6—C1—C8	118.2 (3)	O4—C17—C16	124.2 (3)
C2—C1—C8	124.1 (3)	O4—C17—C18	115.3 (3)
O1—C2—C3	117.4 (3)	C16—C17—C18	120.5 (3)
O1—C2—C1	123.7 (3)	C19—C18—C17	119.2 (3)
C3—C2—C1	118.9 (3)	C19—C18—H18	120.4
C4—C3—C2	120.8 (3)	C17—C18—H18	120.4
C4—C3—H3	119.6	C18—C19—C14	122.5 (4)
C2—C3—H3	119.6	C18—C19—H19	118.8
O2—C4—C3	123.7 (4)	C14—C19—H19	118.8
O2—C4—C5	115.9 (3)	O4—C20—H20A	109.5
C3—C4—C5	120.4 (3)	O4—C20—H20B	109.5
C6—C5—C4	119.1 (3)	H20A—C20—H20B	109.5
C6—C5—H5	120.5	O4—C20—H20C	109.5
C4—C5—H5	120.5	H20A—C20—H20C	109.5
C5—C6—C1	123.1 (4)	H20B—C20—H20C	109.5
C5—C6—H6	118.5	N2—C21—C14	126.9 (3)
C1—C6—H6	118.5	N2—C21—H21	116.5
O2—C7—H7A	109.5	C14—C21—H21	116.5
O2—C7—H7B	109.5	N2—C22—C26	113.1 (3)
H7A—C7—H7B	109.5	N2—C22—C23	118.9 (3)
O2—C7—H7C	109.5	C26—C22—C23	102.7 (3)
H7A—C7—H7C	109.5	N2—C22—H22	107.2
H7B—C7—H7C	109.5	C26—C22—H22	107.2
N1—C8—C1	127.2 (3)	C23—C22—H22	107.2
N1—C8—H8	116.4	C24—C23—C22	104.1 (3)
C1—C8—H8	116.4	C24—C23—H23A	110.9
N1—C9—C13	119.8 (3)	C22—C23—H23A	110.9
N1—C9—C10	112.2 (3)	C24—C23—H23B	110.9
C13—C9—C10	102.8 (3)	C22—C23—H23B	110.9
N1—C9—H9	107.1	H23A—C23—H23B	109.0
C13—C9—H9	107.1	C23—C24—C25	106.2 (3)
C10—C9—H9	107.1	C23—C24—H24A	110.5
C11—C10—C9	105.5 (3)	C25—C24—H24A	110.5
C11—C10—H10A	110.6	C23—C24—H24B	110.5
C9—C10—H10A	110.6	C25—C24—H24B	110.5
C11—C10—H10B	110.6	H24A—C24—H24B	108.7
C9—C10—H10B	110.6	C26—C25—C24	106.0 (3)
H10A—C10—H10B	108.8	C26—C25—H25A	110.5
C12—C11—C10	106.7 (4)	C24—C25—H25A	110.5
C12—C11—H11A	110.4	C26—C25—H25B	110.5
C10—C11—H11A	110.4	C24—C25—H25B	110.5
C12—C11—H11B	110.4	H25A—C25—H25B	108.7
C10—C11—H11B	110.4	C25—C26—C22	102.8 (3)
H11A—C11—H11B	108.6	C25—C26—H26A	111.2
C11—C12—C13	104.6 (3)	C22—C26—H26A	111.2
C11—C12—H12A	110.8	C25—C26—H26B	111.2
C13—C12—H12A	110.8	C22—C26—H26B	111.2
C11—C12—H12B	110.8	H26A—C26—H26B	109.1

Experimental details

Crystal data
Chemical formula	[Cu(C₁₃H₁₆NO₂)₂]
M_r	500.08
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.496 (1), 14.054 (2), 20.442 (2)
β (°)	100.236 (3)
V (Å³)	2402.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.23 × 0.21 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.812, 0.826
No. of measured, independent and observed [I > 2σ(I)] reflections	12222, 4333, 3131
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.163, 1.00
No. of reflections	4333
No. of parameters	300
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −1.16

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—O1	1.890 (2)	Cu1—N2	1.967 (3)
Cu1—O3	1.891 (2)	Cu1—N1	1.978 (3)

O1—Cu1—O3	144.60 (13)	O1—Cu1—N1	95.40 (11)
O1—Cu1—N2	93.93 (11)	O3—Cu1—N1	94.20 (11)
O3—Cu1—N2	95.32 (11)	N2—Cu1—N1	148.66 (12)

Acknowledgements

The authors thank the Scientific Research Foundation of Shaanxi University of Technology (project No. SLGQD0708) for financial support.

References

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