(1H-Imidazole-κN3){N-[1-(2-oxidophenyl-κO)ethyl­idene]-l-phenyl­alaninato-κ2N,O}copper(II)

Han, Y.-J.; Zhao, G.-Q.; Zhao, X.-J.; Song, W.-L.; Shi, J.-L.

doi:10.1107/S160053680802758X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1228

doi:10.1107/S160053680802758X

Open

access

(1H-Imidazole-κN³){N-[1-(2-oxidophenyl-κO)ethylidene]-L-phenylalaninato-κ²N,O}copper(II)

Yong-Jun Han,^a Gan-Qing Zhao,^a ^* Xiao-Jun Zhao,^a Wen-Li Song ^a and Jie-Li Shi ^a

^aSchool of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan 467000, People's Republic of China
^*Correspondence e-mail: zgq1118@163.com

(Received 19 August 2008; accepted 28 August 2008; online 6 September 2008)

In the title compound, [Cu(C₁₇H₁₅NO₃)(C₃H₄N₂)], the Cu^II atom is four-coordinated by two O atoms and the N atom of the tridentate Schiff base ligand, and one N atom from the imidazole ligand in a distorted square-planar geometry. In the crystal structure, molecules are linked into dimers by intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Basu Baul et al. (2007 ); Casella & Guillotti (1983 ); Ganguly et al. (2008 ); Parekh et al. (2006 ); Plesch et al. (1997 ); Usman et al. (2003 ); Vigato & Tamburini (2004 ).

Experimental

Crystal data

[Cu(C₁₇H₁₅NO₃)(C₃H₄N₂)]
M_r = 412.92
Orthorhombic, C 222₁
a = 16.8029 (16) Å
b = 19.8231 (19) Å
c = 11.3642 (11) Å
V = 3785.3 (6) Å³
Z = 8
Mo Kα radiation
μ = 1.18 mm⁻¹
T = 291 (2) K
0.43 × 0.34 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.630, T_max = 0.759
10101 measured reflections
3534 independent reflections
3008 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.067
S = 1.01
3534 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), 1557 Friedel pairs
Flack parameter: −0.029 (12)

Table 1
Selected geometric parameters (Å, °)

Cu1—O1	1.8876 (19)
Cu1—N1	1.945 (2)
Cu1—O3	1.9511 (18)
Cu1—N2	1.958 (2)

O1—Cu1—N1	93.33 (9)
O1—Cu1—O3	171.74 (9)
N1—Cu1—O3	84.90 (8)
O1—Cu1—N2	93.20 (9)
N1—Cu1—N2	162.84 (10)
O3—Cu1—N2	90.77 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3D⋯O2ⁱ	0.86	1.95	2.789 (3)	166
Symmetry code: (i) x, -y+1, -z+2.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); 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: 10.1107/S160053680802758X/ci2661sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802758X/ci2661Isup2.hkl

checkCIF report

Comment top

In the past decades, significant progress has been achieved in understanding the chemistry of transition metal complexes with Schiff base ligands composed of salicylaldehyde, 2-formylpyridine or their analogues, and α-amino acids (Vigato & Tamburini, 2004; Ganguly et al., 2008; Casella & Guillotti, 1983). A few stuctural studies have been performed on Schiff base complexes derived from 2-hydroxyacetophenone and animo acids (Usman et al., 2003; Basu Baul et al., 2007; Parekh et al., 2006). We report here the crystal structure of the title Cu^II complex.

The structure consists of discrete monomeric square-planar Cu^IIcomplex (Fig. 1 and Table 1). The four basal positions are occupied by three donor atoms from the tridentate Schiff base ligand, which furnishes an ONO donor set, with the fourth position occupied by one N atom from the imidazole ligand. The nitrogen heterocycle is planar and it forms an angle of 14.7 (2)° with the C1—C6 ring.

The crystal structure is stabilized by N—H···O type hydrogen bonds (Fig. 2 and Table 2). The H atom attached to N3 is hydrogen-bonded to the neighboring carboxylate oxygen O2 to form a dimer.

Related literature top

For related literature, see: Basu Baul et al. (2007); Casella & Guillotti (1983); Ganguly et al. (2008); Parekh et al. (2006); Plesch et al. (1997); Usman et al. (2003); Vigato & Tamburini (2004).

Experimental top

The title compound was synthesized as described in the literature (Plesch et al., 1997). To L-phenylalanine (1.00 mmol) and potassium hydroxide (1.00 mmol) in 10 ml of methanol was added 2-hydroxyacetophenone (1.00 mmol in 10 ml of methanol) dropwise. The yellow solution was stirred for 2 h at 333 K. The resultant mixture was added dropwise to copper(II) acetate monohydrate (1.00 mmol) and imidazole (1.00 mmol) in an aqueous methanol solution (20 ml, 1:1 v/v), and heated with stirring for 2 h at 333 K. The dark blue solution was filtered and left for several days; the resulting dark blue crystals were filtered off, washed with water, and dried under vacuum.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A view of the crystal packing along the c axis. Hydrogen bonds are shown as dashed lines.

(1H-Imidazole-κN³){N-[1-(2-oxidophenyl-κO)ethylidene]-L- phenylalaninato-κ²N,O}copper(II) top

Crystal data top

[Cu(C₁₇H₁₅NO₃)(C₃H₄N₂)]	F(000) = 1704
M_r = 412.92	D_x = 1.449 Mg m⁻³
Orthorhombic, C222₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c 2	Cell parameters from 3925 reflections
a = 16.8029 (16) Å	θ = 2.4–23.2°
b = 19.8231 (19) Å	µ = 1.18 mm⁻¹
c = 11.3642 (11) Å	T = 291 K
V = 3785.3 (6) Å³	Block, dark blue
Z = 8	0.43 × 0.34 × 0.25 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3534 independent reflections
Radiation source: fine-focus sealed tube	3008 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→16
T_min = 0.630, T_max = 0.759	k = −24→23
10101 measured reflections	l = −13→13

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)] = 0.028	H-atom parameters constrained
wR(F²) = 0.067	w = 1/[σ²(F_o²) + (0.0324P)² + 1.1795P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
3534 reflections	Δρ_max = 0.21 e Å⁻³
245 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1557 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.029 (12)

Crystal data top

[Cu(C₁₇H₁₅NO₃)(C₃H₄N₂)]	V = 3785.3 (6) Å³
M_r = 412.92	Z = 8
Orthorhombic, C222₁	Mo Kα radiation
a = 16.8029 (16) Å	µ = 1.18 mm⁻¹
b = 19.8231 (19) Å	T = 291 K
c = 11.3642 (11) Å	0.43 × 0.34 × 0.25 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3534 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3008 reflections with I > 2σ(I)
T_min = 0.630, T_max = 0.759	R_int = 0.027
10101 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.067	Δρ_max = 0.21 e Å⁻³
S = 1.01	Δρ_min = −0.16 e Å⁻³
3534 reflections	Absolute structure: Flack (1983), 1557 Friedel pairs
245 parameters	Absolute structure parameter: −0.029 (12)
0 restraints

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	0.10619 (2)	0.367615 (16)	0.77896 (3)	0.04364 (11)
N1	0.13985 (13)	0.27457 (10)	0.80032 (19)	0.0406 (5)
N2	0.10665 (16)	0.46531 (10)	0.75384 (17)	0.0459 (5)
N3	0.13752 (15)	0.57138 (11)	0.7787 (3)	0.0547 (6)
H3D	0.1544	0.6078	0.8115	0.066*
O1	0.05861 (14)	0.34996 (10)	0.63167 (17)	0.0624 (6)
O2	0.20326 (14)	0.32527 (10)	1.08596 (17)	0.0577 (6)
O3	0.14173 (11)	0.37985 (8)	0.94100 (15)	0.0470 (5)
C1	0.04519 (18)	0.29043 (15)	0.5868 (2)	0.0485 (7)
C2	0.06894 (17)	0.22761 (15)	0.6360 (2)	0.0461 (7)
C3	0.0429 (2)	0.16858 (17)	0.5793 (3)	0.0615 (9)
H3	0.0564	0.1271	0.6117	0.074*
C4	−0.0015 (2)	0.1697 (2)	0.4781 (4)	0.0778 (11)
H4	−0.0192	0.1296	0.4447	0.093*
C5	−0.0197 (2)	0.2304 (2)	0.4260 (3)	0.0704 (10)
H5	−0.0475	0.2312	0.3553	0.084*
C6	0.0028 (2)	0.28950 (16)	0.4780 (3)	0.0585 (8)
H6	−0.0098	0.3301	0.4416	0.070*
C7	0.11970 (16)	0.22199 (12)	0.7394 (2)	0.0444 (7)
C8	0.15118 (19)	0.15280 (12)	0.7715 (3)	0.0580 (8)
H8A	0.1901	0.1570	0.8328	0.087*
H8B	0.1753	0.1325	0.7035	0.087*
H8C	0.1081	0.1250	0.7984	0.087*
C9	0.19625 (17)	0.27141 (13)	0.8989 (2)	0.0454 (7)
H9	0.1897	0.2284	0.9404	0.054*
C10	0.17829 (18)	0.32911 (13)	0.9830 (2)	0.0439 (7)
C11	0.28234 (18)	0.27726 (15)	0.8539 (3)	0.0563 (8)
H11A	0.3185	0.2738	0.9201	0.068*
H11B	0.2933	0.2398	0.8014	0.068*
C12	0.29811 (17)	0.34248 (14)	0.7897 (3)	0.0520 (7)
C13	0.2807 (2)	0.34864 (17)	0.6704 (3)	0.0656 (10)
H13	0.2606	0.3117	0.6296	0.079*
C14	0.2928 (3)	0.4089 (2)	0.6120 (3)	0.0845 (12)
H14	0.2813	0.4122	0.5321	0.101*
C15	0.3216 (3)	0.4640 (2)	0.6713 (4)	0.0921 (13)
H15	0.3292	0.5047	0.6321	0.110*
C16	0.3390 (3)	0.45879 (18)	0.7879 (5)	0.0925 (14)
H16	0.3589	0.4960	0.8281	0.111*
C17	0.3274 (2)	0.39883 (19)	0.8466 (4)	0.0814 (11)
H17	0.3396	0.3962	0.9263	0.098*
C18	0.13541 (19)	0.51078 (14)	0.8262 (3)	0.0560 (9)
H18	0.1524	0.5013	0.9024	0.067*
C19	0.1082 (2)	0.56540 (16)	0.6691 (3)	0.0731 (10)
H19	0.1025	0.5998	0.6140	0.088*
C20	0.0885 (2)	0.49998 (17)	0.6544 (3)	0.0708 (11)
H20	0.0660	0.4816	0.5868	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0632 (2)	0.03698 (15)	0.03072 (15)	0.00253 (17)	−0.00760 (17)	−0.00122 (14)
N1	0.0497 (13)	0.0383 (11)	0.0339 (13)	0.0008 (10)	0.0026 (10)	−0.0022 (9)
N2	0.0637 (15)	0.0421 (11)	0.0319 (12)	0.0013 (11)	−0.0068 (12)	0.0016 (9)
N3	0.0760 (18)	0.0383 (12)	0.0498 (14)	0.0005 (11)	−0.0040 (14)	0.0027 (12)
O1	0.0910 (16)	0.0539 (14)	0.0424 (11)	−0.0013 (11)	−0.0241 (11)	−0.0035 (10)
O2	0.0849 (16)	0.0513 (12)	0.0368 (10)	0.0122 (11)	−0.0180 (11)	0.0010 (9)
O3	0.0702 (13)	0.0376 (10)	0.0333 (10)	0.0094 (9)	−0.0094 (8)	−0.0010 (8)
C1	0.0508 (18)	0.0605 (19)	0.0342 (15)	−0.0049 (15)	0.0044 (13)	−0.0126 (14)
C2	0.0489 (18)	0.0522 (17)	0.0374 (15)	−0.0067 (14)	0.0086 (13)	−0.0135 (13)
C3	0.062 (2)	0.0598 (19)	0.062 (2)	−0.0079 (16)	0.0073 (17)	−0.0249 (17)
C4	0.070 (2)	0.084 (2)	0.080 (3)	−0.017 (2)	−0.001 (2)	−0.039 (2)
C5	0.057 (2)	0.109 (3)	0.046 (2)	−0.010 (2)	−0.0005 (17)	−0.030 (2)
C6	0.0519 (19)	0.084 (2)	0.0400 (19)	−0.0024 (19)	0.0000 (13)	−0.0078 (18)
C7	0.0538 (18)	0.0392 (13)	0.0400 (16)	−0.0032 (12)	0.0140 (13)	−0.0051 (11)
C8	0.078 (2)	0.0403 (15)	0.0562 (18)	0.0001 (13)	0.0123 (18)	−0.0059 (15)
C9	0.0586 (19)	0.0357 (14)	0.0419 (15)	0.0043 (13)	−0.0051 (14)	0.0034 (12)
C10	0.0550 (19)	0.0377 (15)	0.0391 (15)	−0.0003 (13)	−0.0068 (14)	0.0017 (12)
C11	0.056 (2)	0.0505 (18)	0.063 (2)	0.0117 (15)	−0.0050 (16)	−0.0008 (16)
C12	0.0463 (18)	0.0467 (16)	0.063 (2)	0.0048 (13)	0.0034 (17)	0.0049 (16)
C13	0.082 (3)	0.061 (2)	0.0542 (19)	−0.0013 (17)	0.0195 (18)	−0.0042 (16)
C14	0.115 (3)	0.079 (3)	0.059 (2)	−0.003 (2)	0.022 (2)	0.009 (2)
C15	0.111 (4)	0.065 (3)	0.100 (3)	−0.008 (2)	0.013 (3)	0.018 (2)
C16	0.116 (4)	0.055 (2)	0.107 (4)	−0.026 (2)	−0.029 (3)	0.010 (2)
C17	0.087 (3)	0.073 (2)	0.084 (3)	−0.011 (2)	−0.027 (2)	0.009 (2)
C18	0.088 (3)	0.0427 (16)	0.0375 (16)	0.0023 (15)	−0.0107 (15)	0.0019 (13)
C19	0.108 (3)	0.0540 (19)	0.057 (2)	−0.002 (2)	−0.013 (2)	0.0230 (16)
C20	0.115 (3)	0.0569 (19)	0.0401 (17)	−0.004 (2)	−0.025 (2)	0.0128 (15)

Geometric parameters (Å, º) top

Cu1—O1	1.8876 (19)	C7—C8	1.514 (4)
Cu1—N1	1.945 (2)	C8—H8A	0.96
Cu1—O3	1.9511 (18)	C8—H8B	0.96
Cu1—N2	1.958 (2)	C8—H8C	0.96
N1—C7	1.296 (3)	C9—C10	1.520 (4)
N1—C9	1.469 (3)	C9—C11	1.539 (4)
N2—C18	1.312 (4)	C9—H9	0.98
N2—C20	1.358 (4)	C11—C12	1.508 (4)
N3—C18	1.317 (4)	C11—H11A	0.97
N3—C19	1.346 (4)	C11—H11B	0.97
N3—H3D	0.86	C12—C17	1.381 (4)
O1—C1	1.305 (3)	C12—C13	1.392 (4)
O2—C10	1.246 (3)	C13—C14	1.383 (5)
O3—C10	1.271 (3)	C13—H13	0.93
C1—C2	1.422 (4)	C14—C15	1.371 (6)
C1—C6	1.427 (4)	C14—H14	0.93
C2—C3	1.405 (4)	C15—C16	1.361 (6)
C2—C7	1.457 (4)	C15—H15	0.93
C3—C4	1.371 (5)	C16—C17	1.377 (5)
C3—H3	0.93	C16—H16	0.93
C4—C5	1.376 (5)	C17—H17	0.93
C4—H4	0.93	C18—H18	0.93
C5—C6	1.365 (4)	C19—C20	1.349 (4)
C5—H5	0.93	C19—H19	0.93
C6—H6	0.93	C20—H20	0.93

O1—Cu1—N1	93.33 (9)	H8B—C8—H8C	109.5
O1—Cu1—O3	171.74 (9)	N1—C9—C10	108.6 (2)
N1—Cu1—O3	84.90 (8)	N1—C9—C11	110.4 (2)
O1—Cu1—N2	93.20 (9)	C10—C9—C11	109.8 (2)
N1—Cu1—N2	162.84 (10)	N1—C9—H9	109.3
O3—Cu1—N2	90.77 (8)	C10—C9—H9	109.3
C7—N1—C9	122.8 (2)	C11—C9—H9	109.3
C7—N1—Cu1	128.33 (19)	O2—C10—O3	124.3 (3)
C9—N1—Cu1	108.86 (16)	O2—C10—C9	118.5 (2)
C18—N2—C20	104.9 (2)	O3—C10—C9	117.1 (2)
C18—N2—Cu1	126.11 (19)	C12—C11—C9	113.0 (2)
C20—N2—Cu1	128.4 (2)	C12—C11—H11A	109.0
C18—N3—C19	106.8 (3)	C9—C11—H11A	109.0
C18—N3—H3D	126.6	C12—C11—H11B	109.0
C19—N3—H3D	126.6	C9—C11—H11B	109.0
C1—O1—Cu1	125.97 (19)	H11A—C11—H11B	107.8
C10—O3—Cu1	113.79 (16)	C17—C12—C13	117.4 (3)
O1—C1—C2	126.1 (3)	C17—C12—C11	122.0 (3)
O1—C1—C6	115.9 (3)	C13—C12—C11	120.6 (3)
C2—C1—C6	118.0 (3)	C14—C13—C12	120.8 (3)
C3—C2—C1	117.5 (3)	C14—C13—H13	119.6
C3—C2—C7	119.2 (3)	C12—C13—H13	119.6
C1—C2—C7	123.3 (2)	C15—C14—C13	120.2 (4)
C4—C3—C2	122.7 (4)	C15—C14—H14	119.9
C4—C3—H3	118.6	C13—C14—H14	119.9
C2—C3—H3	118.6	C16—C15—C14	119.6 (4)
C3—C4—C5	119.7 (3)	C16—C15—H15	120.2
C3—C4—H4	120.1	C14—C15—H15	120.2
C5—C4—H4	120.1	C15—C16—C17	120.4 (4)
C6—C5—C4	120.2 (3)	C15—C16—H16	119.8
C6—C5—H5	119.9	C17—C16—H16	119.8
C4—C5—H5	119.9	C16—C17—C12	121.5 (4)
C5—C6—C1	121.6 (3)	C16—C17—H17	119.3
C5—C6—H6	119.2	C12—C17—H17	119.3
C1—C6—H6	119.2	N2—C18—N3	112.3 (3)
N1—C7—C2	121.5 (2)	N2—C18—H18	123.9
N1—C7—C8	120.6 (3)	N3—C18—H18	123.9
C2—C7—C8	117.9 (2)	N3—C19—C20	106.8 (3)
C7—C8—H8A	109.5	N3—C19—H19	126.6
C7—C8—H8B	109.5	C20—C19—H19	126.6
H8A—C8—H8B	109.5	C19—C20—N2	109.2 (3)
C7—C8—H8C	109.5	C19—C20—H20	125.4
H8A—C8—H8C	109.5	N2—C20—H20	125.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3D···O2ⁱ	0.86	1.95	2.789 (3)	166

Symmetry code: (i) x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₇H₁₅NO₃)(C₃H₄N₂)]
M_r	412.92
Crystal system, space group	Orthorhombic, C222₁
Temperature (K)	291
a, b, c (Å)	16.8029 (16), 19.8231 (19), 11.3642 (11)
V (Å³)	3785.3 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.18
Crystal size (mm)	0.43 × 0.34 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.630, 0.759
No. of measured, independent and observed [I > 2σ(I)] reflections	10101, 3534, 3008
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.067, 1.01
No. of reflections	3534
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.16
Absolute structure	Flack (1983), 1557 Friedel pairs
Absolute structure parameter	−0.029 (12)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—O1	1.8876 (19)	Cu1—O3	1.9511 (18)
Cu1—N1	1.945 (2)	Cu1—N2	1.958 (2)

O1—Cu1—N1	93.33 (9)	O1—Cu1—N2	93.20 (9)
O1—Cu1—O3	171.74 (9)	N1—Cu1—N2	162.84 (10)
N1—Cu1—O3	84.90 (8)	O3—Cu1—N2	90.77 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3D···O2ⁱ	0.86	1.95	2.789 (3)	166

Symmetry code: (i) x, −y+1, −z+2.

Acknowledgements

This research was supported by the National Science Foundation of China (grant No. 20676057).

References

Basu Baul, T. S., Masharing, C., Ruisi, G., Jirásko, R., Holčapek, M., Dick, D. V., Wolstenholme, D. & Linden, A. (2007). J. Organomet. Chem. 692, 4849–4862. Web of Science CrossRef CAS Google Scholar
Bruker (2000). SMART and SAINT. Bruker Axs Inc., Madison, Wisconsin, USA. Google Scholar
Casella, L. & Guillotti, M. (1983). Inorg. Chem. 22, 2259–2266. CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ganguly, R., Sreenivasulu, B. & Vittal, J. J. (2008). Coord. Chem. Rev. 252, 1027–1050. Web of Science CrossRef CAS Google Scholar
Parekh, H. M., Mehta, S. R. & Patel, M. N. (2006). Russ. J. Inorg. Chem. 35, 67–72. Web of Science CrossRef Google Scholar
Plesch, G., Friebel, C., Warda, S. A., Sivý, J. & Švajlenová, O. (1997). Transition Met. Chem. 22, 433–440. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Usman, A., Fun, H.-K., Basu Baul, T. S. & Paul, P. C. (2003). Acta Cryst. E59, m438–m440. Web of Science CSD CrossRef IUCr Journals Google Scholar
Vigato, P. A. & Tamburini, S. (2004). Coord. Chem. Rev. 248, 1717–2128. Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.