(2,2′-Bipyridine-κ2N,N′){N-[2-oxido-5-(phenyl­diazen­yl)benzyl­idene-κO]glycinato-κ2N,O}copper(II)

Zhang, Q.-X.; Zhao, G.-Q.; Zhu, J.-Q.; Xue, L.-W.; Han, Y.-J.

doi:10.1107/S1600536809036423

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages m1212-m1213

doi:10.1107/S1600536809036423

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(2,2′-Bipyridine-κ²N,N′){N-[2-oxido-5-(phenyldiazenyl)benzylidene-κO]glycinato-κ²N,O}copper(II)

Qiu-Xia Zhang,^a Gan-Qing Zhao,^a ^* Jian-Qi Zhu,^a Ling-Wei Xue ^a and Yong-Jun Han ^a

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

(Received 18 August 2009; accepted 9 September 2009; online 16 September 2009)

In the title compound, [Cu(C₁₅H₁₁N₃O₃)(C₁₀H₈N₂)], the Cu^II atom is five-coordinated in a distorted square-pyramidal CuN₃O₂ geometry. The basal positions are occupied by three donor atoms from the tridentate Schiff base ligand and by one N atom from the 2,2′-bipyridine ligand. The axial position is occupied by the other N atom of the 2,2′-bipyridine ligand. The crystal structure is consolidated by weak C—H⋯O hydrogen bonds. In addition, π–π interactions between adjacent pyridine rings (centroid–centroid distances = 3.238 and 3.313 Å) may also stabilize the crystal packing.

Related literature

For related structures of copper(II) with Schiff base ligands, see: Raso et al. (1996 , 1999 ); Reddy et al. (2002 ); Wang et al. (2005 ); Warda (1997 , 1998a ,b ,c ). For the synthesis of the ligand, see: Wei et al. (2007 ). For the synthesis of the title compound, see: Plesch et al. (1997 ).

Experimental

Crystal data

[Cu(C₁₅H₁₁N₃O₃)(C₁₀H₈N₂)]
M_r = 500.99
Monoclinic, P 2₁ /c
a = 12.604 (3) Å
b = 12.487 (3) Å
c = 13.962 (3) Å
β = 93.05 (3)°
V = 2194.3 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.820, T_max = 0.820
11072 measured reflections
3882 independent reflections
3331 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.074
S = 1.07
3882 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.9303 (15)
Cu1—N3	1.9354 (17)
Cu1—O2	1.9501 (15)
Cu1—N1	2.0282 (17)
Cu1—N2	2.2392 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯O3ⁱ	0.93	2.56	3.250 (3)	131
C12—H12B⋯O3ⁱⁱ	0.97	2.44	3.365 (3)	160
C4—H4⋯O2ⁱⁱⁱ	0.93	2.50	3.082 (3)	121
Symmetry codes: (i) x, y, z-1; (ii) -x+1, -y, -z+1; (iii) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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/S1600536809036423/wm2250sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036423/wm2250Isup2.hkl

checkCIF report

Comment top

Considerable efforts have been devoted to copper(II) complexes of tridentate Schiff base ligands of the N-alkylidene or N-arylidene aminoacidato type. These compound are interesting in terms of their structural varieties, their electrochemical properties as well as their nature as potential model substances for a number of important biological systems (Raso et al., 1996, 1999). Several stuctural studies have been performed on Schiff base copper(II) complexes derived from salicylaldehyde and animo acids (Reddy et al., 2002; Wang et al., 2005; Warda, 1997, 1998a,b,c). We report here the crystal structure of the title Cu^II complex.

The structure consists of a discrete monomeric square-pyramidal Cu^II complex (Fig. 1 and Table 1). The 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 2, 2'-bipyridine ligand. The axial position is occupied by the other N atom of the 2, 2'-bipyridine igand. The Cu atom is displaced from the O1/O2/N1/N3 basal plane toward the N2 atom by -0.0169 Å.

The 2,2'-bipyridine ligand and the benzene ring (C20···C25) are essentially planar and form a dihedral angle of 92.5° and 15.8°, respectively, with the benzene ring of the Schiff base ligand.

The crystal structure is stabilized by weak hydrogen bonds, such as C4—H4···O2 (3.082 Å), C3—H3···O1 (3.365 Å) and C25—H25···O3 (3.250 Å). The π-π interactions between the adjacent pyridine rings [C1···C9 (3.238 Å) and C2···C10 (3.313 Å)] play important role in the stability of the complex (Fig. 2 and Table 2).

Related literature top

For related structures of copper(II) with Schiff base ligands, see: Raso et al. (1996, 1999); Reddy et al. (2002); Wang et al. (2005); Warda (1997, 1998a,b,c). For the synthesis of the ligand, see: Wei et al. (2007). For the synthesis of the title compound, see: Plesch et al. (1997).

Experimental top

The compound of 5-(phenyldiazenyl)salicylaldehyde was synthesized as described in the literature (Wei et al., 2007). The title compound was synthesized as described in the literature (Plesch et al., 1997): To glycine (1.00 mmol) and potassium hydroxide (1.00 mmol) in 10 ml of methanol was added 5-(phenyldiazenyl)salicylaldehyde (1.00 mmol) in 30 ml of dimethylfomamide dropwise. The yellowish-brown solution was stirred for 2.0 h at 333 K. The resultant mixture was added dropwise to copper(II) acetate monohydrate (1.00 mmol) and 2, 2'-bipyridine (1.00 mmol) in 10 ml of methanol, and heated with stirring for 2.0 h at 333 K. The dark green solution was filtered and left for several days. Dark-green crystals had formed that were filtered off, washed with water, and dried under vacuum.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A view of the crystal packing along the a axis. Hydrogen bonds are shown as dashed lines.

(2,2'-Bipyridine-κ²N,N'){N-[5-(phenyldiazenyl)salicylidene]glycinato-κ³N,O,O'}copper(II) top

Crystal data top

[Cu(C₁₅H₁₁N₃O₃)(C₁₀H₈N₂)]	F(000) = 1028
M_r = 500.99	D_x = 1.516 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5614 reflections
a = 12.604 (3) Å	θ = 2.2–27.5°
b = 12.487 (3) Å	µ = 1.03 mm⁻¹
c = 13.962 (3) Å	T = 296 K
β = 93.05 (3)°	Block, dark green
V = 2194.3 (9) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3882 independent reflections
Radiation source: fine-focus sealed tube	3331 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 25.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→10
T_min = 0.820, T_max = 0.820	k = −14→14
11072 measured reflections	l = −16→16

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0343P)² + 0.837P] where P = (F_o² + 2F_c²)/3
3882 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Cu(C₁₅H₁₁N₃O₃)(C₁₀H₈N₂)]	V = 2194.3 (9) Å³
M_r = 500.99	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.604 (3) Å	µ = 1.03 mm⁻¹
b = 12.487 (3) Å	T = 296 K
c = 13.962 (3) Å	0.20 × 0.20 × 0.20 mm
β = 93.05 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3882 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3331 reflections with I > 2σ(I)
T_min = 0.820, T_max = 0.820	R_int = 0.020
11072 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.07	Δρ_max = 0.21 e Å⁻³
3882 reflections	Δρ_min = −0.36 e Å⁻³
307 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	0.192784 (18)	−0.04691 (2)	0.315857 (17)	0.03322 (9)
C1	0.09307 (19)	0.18579 (18)	0.36777 (16)	0.0465 (5)
H1	0.1606	0.2138	0.3609	0.056*
C2	0.0121 (2)	0.2551 (2)	0.38779 (17)	0.0522 (6)
H2	0.0247	0.3282	0.3942	0.063*
C3	−0.0875 (2)	0.2136 (2)	0.39801 (17)	0.0555 (6)
H3	−0.1437	0.2586	0.4112	0.067*
C4	−0.10356 (18)	0.1052 (2)	0.38851 (16)	0.0469 (6)
H4	−0.1706	0.0759	0.3953	0.056*
C5	−0.01873 (16)	0.04031 (17)	0.36876 (14)	0.0356 (5)
C6	−0.02777 (16)	−0.07837 (17)	0.36193 (14)	0.0367 (5)
C7	−0.12214 (18)	−0.1328 (2)	0.37705 (17)	0.0513 (6)
H7	−0.1840	−0.0951	0.3881	0.062*
C8	−0.1224 (2)	−0.2431 (2)	0.37532 (18)	0.0571 (7)
H8	−0.1848	−0.2804	0.3847	0.069*
C9	−0.0307 (2)	−0.29785 (19)	0.35978 (16)	0.0493 (6)
H9	−0.0295	−0.3723	0.3599	0.059*
C10	0.05944 (18)	−0.23985 (17)	0.34394 (14)	0.0414 (5)
H10	0.1218	−0.2767	0.3329	0.050*
C11	0.32869 (16)	−0.00987 (18)	0.47223 (15)	0.0380 (5)
C12	0.38063 (17)	0.05212 (17)	0.39264 (14)	0.0386 (5)
H12A	0.3773	0.1284	0.4055	0.046*
H12B	0.4548	0.0318	0.3907	0.046*
C13	0.36753 (16)	0.04938 (16)	0.22099 (14)	0.0344 (5)
H13	0.4359	0.0775	0.2242	0.041*
C14	0.31658 (16)	0.03250 (15)	0.12687 (14)	0.0321 (4)
C15	0.37072 (17)	0.06897 (17)	0.04804 (14)	0.0368 (5)
H15	0.4385	0.0977	0.0582	0.044*
C16	0.32614 (17)	0.06347 (16)	−0.04450 (14)	0.0380 (5)
C17	0.22613 (18)	0.01671 (18)	−0.05992 (15)	0.0436 (5)
H17	0.1961	0.0110	−0.1220	0.052*
C18	0.17160 (18)	−0.02104 (18)	0.01584 (15)	0.0414 (5)
H18	0.1052	−0.0521	0.0037	0.050*
C19	0.21339 (16)	−0.01413 (16)	0.11159 (14)	0.0329 (4)
C20	0.50636 (17)	0.19390 (17)	−0.19420 (14)	0.0380 (5)
C21	0.59128 (18)	0.26270 (19)	−0.17756 (16)	0.0474 (6)
H21	0.6141	0.2804	−0.1151	0.057*
C22	0.64230 (19)	0.3052 (2)	−0.25454 (18)	0.0547 (6)
H22	0.6985	0.3527	−0.2438	0.066*
C23	0.60982 (19)	0.2772 (2)	−0.34675 (17)	0.0512 (6)
H23	0.6447	0.3053	−0.3982	0.061*
C24	0.52609 (19)	0.20795 (19)	−0.36326 (16)	0.0469 (6)
H24	0.5049	0.1891	−0.4258	0.056*
C25	0.47297 (18)	0.16593 (18)	−0.28733 (15)	0.0426 (5)
H25	0.4158	0.1197	−0.2986	0.051*
N1	0.06132 (13)	−0.13269 (13)	0.34377 (11)	0.0337 (4)
N2	0.07904 (14)	0.08041 (14)	0.35774 (12)	0.0387 (4)
N3	0.32500 (13)	0.02827 (13)	0.30014 (11)	0.0322 (4)
N4	0.37471 (15)	0.10262 (15)	−0.12741 (12)	0.0440 (4)
N5	0.45784 (15)	0.15498 (15)	−0.11024 (12)	0.0421 (4)
O1	0.15568 (11)	−0.04915 (11)	0.17994 (10)	0.0393 (3)
O2	0.25223 (12)	−0.07232 (13)	0.44568 (10)	0.0437 (4)
O3	0.36149 (13)	0.00378 (16)	0.55548 (11)	0.0560 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02967 (15)	0.03941 (16)	0.03078 (14)	−0.00550 (10)	0.00342 (10)	0.00006 (10)
C1	0.0491 (14)	0.0435 (14)	0.0464 (13)	−0.0057 (11)	−0.0006 (10)	−0.0030 (10)
C2	0.0697 (17)	0.0393 (13)	0.0475 (13)	0.0076 (12)	0.0005 (12)	−0.0042 (10)
C3	0.0613 (17)	0.0569 (16)	0.0491 (14)	0.0210 (13)	0.0113 (12)	0.0023 (12)
C4	0.0420 (13)	0.0571 (16)	0.0426 (13)	0.0055 (11)	0.0105 (10)	0.0074 (11)
C5	0.0351 (11)	0.0443 (12)	0.0275 (10)	0.0011 (9)	0.0040 (8)	0.0025 (9)
C6	0.0364 (11)	0.0469 (12)	0.0267 (10)	−0.0055 (9)	0.0024 (8)	0.0019 (9)
C7	0.0367 (12)	0.0621 (16)	0.0558 (14)	−0.0076 (11)	0.0098 (11)	0.0021 (12)
C8	0.0506 (15)	0.0612 (17)	0.0600 (16)	−0.0252 (13)	0.0065 (12)	0.0030 (13)
C9	0.0635 (16)	0.0422 (13)	0.0423 (13)	−0.0164 (12)	0.0023 (11)	0.0004 (10)
C10	0.0484 (13)	0.0409 (13)	0.0350 (11)	−0.0052 (10)	0.0031 (10)	−0.0009 (9)
C11	0.0321 (11)	0.0486 (13)	0.0333 (11)	0.0042 (10)	0.0031 (9)	0.0010 (9)
C12	0.0359 (11)	0.0458 (13)	0.0338 (11)	−0.0063 (9)	−0.0017 (9)	−0.0021 (9)
C13	0.0293 (10)	0.0367 (11)	0.0374 (11)	−0.0036 (9)	0.0033 (9)	0.0020 (9)
C14	0.0327 (11)	0.0314 (11)	0.0324 (10)	0.0018 (8)	0.0036 (8)	0.0009 (8)
C15	0.0353 (11)	0.0395 (12)	0.0358 (11)	−0.0046 (9)	0.0055 (9)	−0.0006 (9)
C16	0.0456 (13)	0.0366 (12)	0.0323 (11)	−0.0002 (9)	0.0072 (9)	0.0001 (9)
C17	0.0490 (14)	0.0506 (14)	0.0307 (11)	−0.0055 (11)	−0.0007 (10)	−0.0018 (9)
C18	0.0416 (12)	0.0456 (13)	0.0366 (11)	−0.0094 (10)	−0.0010 (9)	−0.0017 (9)
C19	0.0351 (11)	0.0295 (10)	0.0343 (11)	0.0004 (8)	0.0037 (9)	−0.0021 (8)
C20	0.0416 (12)	0.0392 (12)	0.0340 (11)	0.0052 (9)	0.0085 (9)	0.0012 (9)
C21	0.0454 (13)	0.0555 (15)	0.0413 (12)	−0.0025 (11)	0.0034 (10)	−0.0030 (11)
C22	0.0415 (13)	0.0637 (16)	0.0594 (16)	−0.0094 (12)	0.0083 (11)	0.0035 (12)
C23	0.0496 (14)	0.0568 (15)	0.0488 (14)	0.0030 (12)	0.0178 (11)	0.0109 (11)
C24	0.0580 (15)	0.0499 (14)	0.0334 (11)	0.0053 (11)	0.0083 (10)	0.0026 (10)
C25	0.0471 (13)	0.0427 (12)	0.0385 (12)	−0.0026 (10)	0.0054 (10)	−0.0002 (10)
N1	0.0341 (9)	0.0380 (10)	0.0291 (8)	−0.0038 (7)	0.0028 (7)	0.0005 (7)
N2	0.0374 (10)	0.0401 (10)	0.0387 (10)	−0.0021 (8)	0.0028 (8)	−0.0028 (8)
N3	0.0300 (9)	0.0365 (10)	0.0299 (9)	−0.0018 (7)	0.0002 (7)	0.0007 (7)
N4	0.0503 (11)	0.0494 (11)	0.0329 (9)	−0.0043 (9)	0.0081 (8)	0.0009 (8)
N5	0.0479 (11)	0.0448 (11)	0.0343 (10)	−0.0015 (9)	0.0087 (8)	0.0003 (8)
O1	0.0357 (8)	0.0498 (9)	0.0325 (7)	−0.0130 (7)	0.0039 (6)	0.0001 (6)
O2	0.0373 (8)	0.0599 (10)	0.0339 (8)	−0.0103 (7)	0.0030 (6)	0.0062 (7)
O3	0.0504 (10)	0.0857 (13)	0.0313 (8)	−0.0114 (9)	−0.0034 (7)	0.0015 (8)

Geometric parameters (Å, º) top

Cu1—O1	1.9303 (15)	C12—H12A	0.9700
Cu1—N3	1.9354 (17)	C12—H12B	0.9700
Cu1—O2	1.9501 (15)	C13—N3	1.281 (3)
Cu1—N1	2.0282 (17)	C13—C14	1.447 (3)
Cu1—N2	2.2392 (18)	C13—H13	0.9300
C1—N2	1.334 (3)	C14—C15	1.402 (3)
C1—C2	1.377 (3)	C14—C19	1.431 (3)
C1—H1	0.9300	C15—C16	1.383 (3)
C2—C3	1.373 (3)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.395 (3)
C3—C4	1.375 (4)	C16—N4	1.424 (3)
C3—H3	0.9300	C17—C18	1.375 (3)
C4—C5	1.381 (3)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.413 (3)
C5—N2	1.347 (3)	C18—H18	0.9300
C5—C6	1.489 (3)	C19—O1	1.306 (2)
C6—N1	1.347 (3)	C20—C21	1.382 (3)
C6—C7	1.395 (3)	C20—C25	1.390 (3)
C7—C8	1.378 (4)	C20—N5	1.435 (3)
C7—H7	0.9300	C21—C22	1.387 (3)
C8—C9	1.370 (4)	C21—H21	0.9300
C8—H8	0.9300	C22—C23	1.375 (3)
C9—C10	1.375 (3)	C22—H22	0.9300
C9—H9	0.9300	C23—C24	1.375 (3)
C10—N1	1.338 (3)	C23—H23	0.9300
C10—H10	0.9300	C24—C25	1.387 (3)
C11—O3	1.225 (2)	C24—H24	0.9300
C11—O2	1.279 (3)	C25—H25	0.9300
C11—C12	1.530 (3)	N4—N5	1.247 (2)
C12—N3	1.467 (3)

O1—Cu1—N3	93.47 (7)	C14—C13—H13	117.7
O1—Cu1—O2	166.50 (7)	C15—C14—C19	119.47 (18)
N3—Cu1—O2	83.90 (7)	C15—C14—C13	117.05 (18)
O1—Cu1—N1	91.35 (6)	C19—C14—C13	123.42 (17)
N3—Cu1—N1	174.37 (7)	C16—C15—C14	121.80 (19)
O2—Cu1—N1	90.74 (7)	C16—C15—H15	119.1
O1—Cu1—N2	98.17 (7)	C14—C15—H15	119.1
N3—Cu1—N2	104.62 (7)	C15—C16—C17	118.92 (19)
O2—Cu1—N2	95.31 (7)	C15—C16—N4	124.85 (19)
N1—Cu1—N2	77.52 (7)	C17—C16—N4	116.23 (19)
N2—C1—C2	123.0 (2)	C18—C17—C16	120.6 (2)
N2—C1—H1	118.5	C18—C17—H17	119.7
C2—C1—H1	118.5	C16—C17—H17	119.7
C3—C2—C1	118.4 (2)	C17—C18—C19	122.0 (2)
C3—C2—H2	120.8	C17—C18—H18	119.0
C1—C2—H2	120.8	C19—C18—H18	119.0
C2—C3—C4	119.5 (2)	O1—C19—C18	118.48 (18)
C2—C3—H3	120.3	O1—C19—C14	124.38 (18)
C4—C3—H3	120.3	C18—C19—C14	117.13 (18)
C3—C4—C5	119.1 (2)	C21—C20—C25	120.44 (19)
C3—C4—H4	120.5	C21—C20—N5	115.65 (19)
C5—C4—H4	120.5	C25—C20—N5	123.9 (2)
N2—C5—C4	121.9 (2)	C20—C21—C22	119.6 (2)
N2—C5—C6	115.48 (18)	C20—C21—H21	120.2
C4—C5—C6	122.6 (2)	C22—C21—H21	120.2
N1—C6—C7	120.6 (2)	C23—C22—C21	120.1 (2)
N1—C6—C5	116.83 (17)	C23—C22—H22	120.0
C7—C6—C5	122.5 (2)	C21—C22—H22	120.0
C8—C7—C6	119.0 (2)	C24—C23—C22	120.3 (2)
C8—C7—H7	120.5	C24—C23—H23	119.9
C6—C7—H7	120.5	C22—C23—H23	119.9
C9—C8—C7	120.1 (2)	C23—C24—C25	120.5 (2)
C9—C8—H8	120.0	C23—C24—H24	119.7
C7—C8—H8	120.0	C25—C24—H24	119.7
C8—C9—C10	118.3 (2)	C24—C25—C20	119.1 (2)
C8—C9—H9	120.9	C24—C25—H25	120.5
C10—C9—H9	120.9	C20—C25—H25	120.5
N1—C10—C9	122.8 (2)	C10—N1—C6	119.21 (18)
N1—C10—H10	118.6	C10—N1—Cu1	122.89 (15)
C9—C10—H10	118.6	C6—N1—Cu1	117.90 (14)
O3—C11—O2	124.8 (2)	C1—N2—C5	118.15 (19)
O3—C11—C12	118.9 (2)	C1—N2—Cu1	130.14 (15)
O2—C11—C12	116.29 (18)	C5—N2—Cu1	111.61 (14)
N3—C12—C11	109.50 (17)	C13—N3—C12	121.03 (17)
N3—C12—H12A	109.8	C13—N3—Cu1	126.86 (14)
C11—C12—H12A	109.8	C12—N3—Cu1	111.89 (12)
N3—C12—H12B	109.8	N5—N4—C16	114.62 (18)
C11—C12—H12B	109.8	N4—N5—C20	114.24 (18)
H12A—C12—H12B	108.2	C19—O1—Cu1	126.76 (13)
N3—C13—C14	124.59 (18)	C11—O2—Cu1	114.61 (13)
N3—C13—H13	117.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···O3ⁱ	0.93	2.56	3.250 (3)	131
C12—H12B···O3ⁱⁱ	0.97	2.44	3.365 (3)	160
C4—H4···O2ⁱⁱⁱ	0.93	2.50	3.082 (3)	121

Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y, −z+1; (iii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₅H₁₁N₃O₃)(C₁₀H₈N₂)]
M_r	500.99
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.604 (3), 12.487 (3), 13.962 (3)
β (°)	93.05 (3)
V (Å³)	2194.3 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.820, 0.820
No. of measured, independent and observed [I > 2σ(I)] reflections	11072, 3882, 3331
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.074, 1.07
No. of reflections	3882
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.36

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

Selected bond lengths (Å) top

Cu1—O1	1.9303 (15)	Cu1—N1	2.0282 (17)
Cu1—N3	1.9354 (17)	Cu1—N2	2.2392 (18)
Cu1—O2	1.9501 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···O3ⁱ	0.93	2.56	3.250 (3)	131.0
C12—H12B···O3ⁱⁱ	0.97	2.44	3.365 (3)	160.1
C4—H4···O2ⁱⁱⁱ	0.93	2.50	3.082 (3)	121.1

Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y, −z+1; (iii) −x, −y, −z+1.

Acknowledgements

This research was supported by the National Sciences Foundation of China (No. 20877036) and the High-Level Personnel Foundation of Pingdingshan University (No. 2009001).

References

Bruker (2008). APEX2 and SAINT. Bruker Axs Inc., Madison, Wisconsin, USA. 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
Raso, A. G., Fiol, J. J., Badenas, F. & Quiros, M. (1996). Polyhedron, 18, 4407–4413. CSD CrossRef Web of Science Google Scholar
Raso, A. G., Fiol, J. J., Zafra, A. L., Cabrero, A., Mata, I. & Molins, E. (1999). Polyhedron, 18, 871–878. Web of Science CSD CrossRef Google Scholar
Reddy, P. A. N., Nethaji, M. & Chakravarty, A. R. (2002). Inorg. Chim. Acta, 337, 450–458. Web of Science CSD CrossRef CAS 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
Wang, M. Z., Cai, G. L., Meng, Z. X. & Liu, B. L. (2005). J. Chem. Crystallogr. 35, 43–47. Web of Science CSD CrossRef Google Scholar
Warda, S. A. (1997). Acta Cryst. C53, 1759–1761. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Warda, S. A. (1998a). Acta Cryst. C54, 1754–1755. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Warda, S. A. (1998b). Acta Cryst. C54, 187–189. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Warda, S. A. (1998c). Acta Cryst. C54, 768–770. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Wei, T. B., Guo, X. D., Wang, J. & Zhang, Y. M. (2007). Chin. J. Org. Chem. 27, 1121–1125. CAS Google Scholar

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