[2-Hydroxy-N′-(4-oxo-4-phenyl­butan-2-yl­idene)benzohydrazidato(2−)]pyridine­copper(II)

Zhang, S.-P.; Wei, Y.; Shao, S.-C.

doi:10.1107/S1600536810047719

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1635

https://doi.org/10.1107/S1600536810047719

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[2-Hydroxy-N′-(4-oxo-4-phenylbutan-2-ylidene)benzohydrazidato(2−)]pyridinecopper(II)

Shu-Ping Zhang,^a Ying Wei ^a and Si-Chang Shao ^a ^*

^aDepartment of Chemistry, Fuyang Normal College, Fuyang, Anhui 236041, People's Republic of China
^*Correspondence e-mail: shaosic@fync.edu.cn

(Received 28 October 2010; accepted 17 November 2010; online 24 November 2010)

The mononuclear title complex, [Cu(C₁₇H₁₄N₂O₃)(C₅H₅N)], was synthesized by the reaction of CuCl₂·2H₂O with N-(4-oxo-4-phenylbutan-2-ylidene)benzohydrazide (H₂L). The central Cu^II atom exhibits a distorted square-planar coordination geometry, defined by two O atoms, one N atom from the ligand and one pyridine N atom with Cu—N distances of 1.874 (4) and 1.963 (4) Å, while the Cu—O distances are 1.857 (3) and 1.890 (3) Å. An intramolecular O—H⋯N interaction occurs.

Related literature

For the biological properties of Schiff base–metal complexes, see: Cozzi (2004 ). For metallobiomolecules, see: Singh et al. (2007 ). For metal ions bonded to biologically active compounds, see: Canpolat & Kaya (2004 ); Yildiz et al. (2004 ). For a related structure, see: Shen et al. (1997 ).

Experimental

Crystal data

[Cu(C₁₇H₁₄N₂O₃)(C₅H₅N)]
M_r = 436.94
Orthorhombic, C 222₁
a = 7.7096 (8) Å
b = 22.906 (2) Å
c = 20.983 (2) Å
V = 3705.6 (7) Å³
Z = 8
Mo Kα radiation
μ = 1.21 mm⁻¹
T = 298 K
0.28 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.728, T_max = 0.794
13526 measured reflections
4034 independent reflections
3340 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.131
S = 1.08
4034 reflections
252 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.56 e Å⁻³
Absolute structure: Flack (1983 ), 1761 Friedel pairs
Flack parameter: 0.08 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.78	2.500 (5)	146

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); 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/S1600536810047719/bx2325sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810047719/bx2325Isup2.hkl

checkCIF report

Comment top

Schiff base metal complexes have been widely studied because they have industrial, antifungal, antibacterial, anticancer and herbicidal applications (Cozzi, 2004). It is well known that N atoms play a key role in the coordination of metals at the active sites of numerous metallobiomolecules (Singh, et al., 2007). They serve as models for biological important species and find applications in biomimetic catalytic reactions. Chelating ligands containing N and O donor atoms show broad biological activity and are of special interest because of the variety of ways in which they are bonded to metal ions. It is known that the existence of metal ions bonded to biologically active compounds may enhance their activities (Canpolat, et al., 2004; Yildiz, et al., 2004). Therefore, it is an important study to design and synthesis of new multidentate ligands cotaining N and O atoms and apply to synthesize complexes.

The asymmetric unit is composed of one mononuclear complex, (Fig.1). The central Cu^II atom exhibits a distorted square-plannar coordination geometry, defined by two O atoms, one N atom from the ligand molecule and one N atom of the pyridine molecule with Cu—N distances of 1.874 (4) and 1.963 (4) Å while Cu—O distances are 1.857 (3) and 1.890 (3) Å respectively. The Cu—N and Cu—O distances are comparable to those found in other crystallographically characterized Cu^II complex (Shen, et al. 1997). The crystal structure of the title compound is stabilized by one intramolecular O—H···N interactions with average H···N distances 1.78Å and O—H···N angle 146.3°.

Related literature top

For the biological properties of Schiff base–metal complexes, see: Cozzi (2004). For metallobiomolecules, see: Singh et al. (2007). For metal ions bonded to biologically active compounds, see: Canpolat et al. (2004); Yildiz et al. (2004). For a related structure, see: Shen et al. (1997).

Experimental top

All reagents and solvents were used as obtained commercially without further purification. CuCl₂.2H₂O (0.170 mg, 0.1 mmol) was dissolved in 6 ml deionized water, giving a transparent solution, and 1 mL pyridine solution dissolved with L (28.2 mg, 0.1 mmol) was dropwised for 0.5 h. After stirring for 8 h, the solution was filtered. Black single crystals of the title compound were obtained from the filtrate after 3 weeks. Analysis calculated (%): C, 60.47; H, 4.38; N, 9.62%; Found: C, 60.15; H, 4.59; N, 9.49%.

Structure description top

For the biological properties of Schiff base–metal complexes, see: Cozzi (2004). For metallobiomolecules, see: Singh et al. (2007). For metal ions bonded to biologically active compounds, see: Canpolat et al. (2004); Yildiz et al. (2004). For a related structure, see: Shen et al. (1997).

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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.

[2-Hydroxy-N'-(4-oxo-4-phenylbutan-2- ylidene)benzohydrazidato(2-)]pyridinecopper(II) top

Crystal data top

[Cu(C₁₇H₁₄N₂O₃)(C₅H₅N)]	F(000) = 1800
M_r = 436.94	D_x = 1.566 Mg m⁻³
Orthorhombic, C222₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c 2	Cell parameters from 3542 reflections
a = 7.7096 (8) Å	θ = 2.1–23.1°
b = 22.906 (2) Å	µ = 1.21 mm⁻¹
c = 20.983 (2) Å	T = 298 K
V = 3705.6 (7) Å³	Block, dark green
Z = 8	0.28 × 0.20 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	4034 independent reflections
Radiation source: fine-focus sealed tube	3340 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
phi and ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.728, T_max = 0.794	k = −29→27
13526 measured reflections	l = −26→26

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)] = 0.057	H-atom parameters constrained
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0614P)² + 1.8583P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.003
4034 reflections	Δρ_max = 0.45 e Å⁻³
252 parameters	Δρ_min = −0.56 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1761 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (3)

Crystal data top

[Cu(C₁₇H₁₄N₂O₃)(C₅H₅N)]	V = 3705.6 (7) Å³
M_r = 436.94	Z = 8
Orthorhombic, C222₁	Mo Kα radiation
a = 7.7096 (8) Å	µ = 1.21 mm⁻¹
b = 22.906 (2) Å	T = 298 K
c = 20.983 (2) Å	0.28 × 0.20 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	4034 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3340 reflections with I > 2σ(I)
T_min = 0.728, T_max = 0.794	R_int = 0.050
13526 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.131	Δρ_max = 0.45 e Å⁻³
S = 1.08	Δρ_min = −0.56 e Å⁻³
4034 reflections	Absolute structure: Flack (1983), 1761 Friedel pairs
252 parameters	Absolute structure parameter: 0.08 (3)
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	0.26164 (7)	0.56424 (2)	0.75389 (2)	0.03955 (17)
C1	0.4395 (6)	0.4324 (2)	0.8613 (2)	0.0396 (11)
C2	0.5248 (7)	0.4551 (2)	0.9121 (2)	0.0496 (13)
H2	0.5322	0.4955	0.9165	0.059*
C3	0.5994 (7)	0.4205 (3)	0.9567 (2)	0.0558 (14)
H3	0.6569	0.4370	0.9913	0.067*
C4	0.5895 (8)	0.3611 (3)	0.9504 (3)	0.0653 (17)
H4	0.6401	0.3369	0.9807	0.078*
C5	0.5071 (9)	0.3384 (2)	0.9008 (2)	0.0534 (12)
H5	0.5021	0.2980	0.8964	0.064*
C6	0.4294 (7)	0.3728 (2)	0.8558 (2)	0.0440 (12)
C7	0.3627 (6)	0.4715 (2)	0.8143 (2)	0.0386 (11)
C8	0.0179 (5)	0.60424 (13)	0.58645 (12)	0.0411 (11)
C9	0.0827 (5)	0.66043 (14)	0.57885 (14)	0.0524 (13)
H9A	0.1631	0.6751	0.6078	0.063*
C10	0.0275 (5)	0.69465 (12)	0.52805 (16)	0.0589 (15)
H10A	0.0709	0.7322	0.5230	0.071*
C11	−0.0925 (5)	0.67268 (15)	0.48484 (14)	0.0617 (16)
H11A	−0.1295	0.6956	0.4509	0.074*
C12	−0.1574 (4)	0.61649 (16)	0.49245 (15)	0.0614 (15)
H12A	−0.2377	0.6018	0.4635	0.074*
C13	−0.1022 (5)	0.58227 (12)	0.54325 (16)	0.0589 (15)
H13A	−0.1456	0.5447	0.5483	0.071*
C14	0.0822 (6)	0.5682 (2)	0.6383 (2)	0.0423 (11)
C15	0.0672 (6)	0.5104 (2)	0.6359 (2)	0.0435 (12)
H15	0.0074	0.4954	0.6011	0.052*
C16	0.1308 (6)	0.4698 (2)	0.6795 (2)	0.0391 (11)
C17	0.1033 (7)	0.4076 (2)	0.6673 (2)	0.0476 (12)
H17A	0.0384	0.3908	0.7017	0.071*
H17B	0.2134	0.3883	0.6638	0.071*
H17C	0.0399	0.4029	0.6282	0.071*
C18	0.3924 (7)	0.6464 (2)	0.8448 (2)	0.0532 (14)
H18	0.4366	0.6128	0.8636	0.064*
C19	0.4202 (9)	0.6974 (3)	0.8736 (3)	0.0635 (17)
H19	0.4847	0.6989	0.9110	0.076*
C20	0.3560 (11)	0.7459 (3)	0.8488 (3)	0.080 (2)
H20	0.3752	0.7818	0.8682	0.096*
C21	0.2630 (12)	0.7419 (2)	0.7953 (3)	0.085 (2)
H21	0.2139	0.7750	0.7771	0.102*
C22	0.2413 (9)	0.6887 (2)	0.7680 (2)	0.0658 (17)
H22	0.1769	0.6862	0.7307	0.079*
N1	0.2780 (5)	0.44657 (14)	0.76881 (16)	0.0376 (8)
N2	0.2134 (4)	0.48748 (16)	0.72866 (15)	0.0353 (8)
N3	0.3066 (5)	0.64115 (17)	0.79176 (17)	0.0400 (9)
O1	0.3475 (6)	0.34649 (15)	0.80904 (17)	0.0602 (10)
H1	0.3070	0.3710	0.7848	0.090*
O2	0.3808 (5)	0.52533 (13)	0.82017 (15)	0.0428 (8)
O3	0.1558 (5)	0.59686 (14)	0.68281 (15)	0.0499 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0412 (3)	0.0412 (3)	0.0363 (3)	0.0042 (3)	−0.0104 (3)	−0.0039 (2)
C1	0.034 (2)	0.045 (3)	0.039 (2)	0.004 (2)	0.0083 (18)	0.008 (2)
C2	0.058 (4)	0.050 (3)	0.041 (3)	0.005 (3)	0.000 (2)	−0.002 (2)
C3	0.059 (4)	0.066 (4)	0.043 (3)	0.008 (3)	−0.006 (2)	0.007 (2)
C4	0.056 (4)	0.085 (5)	0.055 (3)	0.014 (4)	0.005 (3)	0.027 (3)
C5	0.058 (3)	0.050 (3)	0.052 (3)	0.007 (3)	0.010 (3)	0.011 (2)
C6	0.050 (3)	0.041 (3)	0.041 (3)	0.006 (2)	0.014 (2)	−0.003 (2)
C7	0.030 (2)	0.050 (3)	0.036 (2)	0.002 (2)	−0.004 (2)	−0.004 (2)
C8	0.035 (3)	0.058 (3)	0.031 (2)	0.005 (3)	−0.005 (2)	−0.008 (2)
C9	0.060 (3)	0.056 (3)	0.041 (3)	0.003 (3)	−0.004 (2)	−0.005 (2)
C10	0.064 (4)	0.061 (3)	0.052 (3)	0.005 (3)	−0.001 (3)	0.003 (3)
C11	0.064 (4)	0.082 (5)	0.039 (3)	0.018 (3)	−0.002 (3)	−0.002 (3)
C12	0.058 (3)	0.075 (4)	0.051 (3)	0.007 (3)	−0.018 (3)	0.007 (3)
C13	0.049 (3)	0.074 (4)	0.054 (3)	0.006 (3)	−0.021 (3)	0.003 (3)
C14	0.034 (2)	0.056 (3)	0.036 (2)	0.012 (3)	−0.0044 (19)	−0.003 (2)
C15	0.040 (3)	0.057 (3)	0.034 (2)	−0.002 (2)	−0.008 (2)	−0.013 (2)
C16	0.032 (2)	0.042 (3)	0.043 (2)	−0.002 (2)	0.007 (2)	−0.009 (2)
C17	0.050 (3)	0.047 (3)	0.046 (3)	−0.004 (3)	−0.011 (2)	−0.008 (2)
C18	0.061 (4)	0.051 (3)	0.048 (3)	0.003 (3)	−0.019 (3)	−0.007 (2)
C19	0.084 (4)	0.049 (3)	0.057 (3)	0.007 (3)	−0.026 (3)	−0.006 (3)
C20	0.124 (7)	0.044 (3)	0.072 (4)	0.005 (4)	−0.018 (4)	−0.013 (3)
C21	0.133 (7)	0.045 (3)	0.078 (4)	0.028 (4)	−0.036 (5)	−0.012 (3)
C22	0.097 (5)	0.053 (3)	0.048 (3)	0.014 (4)	−0.028 (4)	0.002 (2)
N1	0.038 (2)	0.0335 (19)	0.0408 (17)	0.0034 (16)	0.0008 (17)	0.0041 (14)
N2	0.0283 (19)	0.045 (2)	0.0327 (16)	0.0030 (16)	0.0005 (15)	−0.0042 (15)
N3	0.043 (2)	0.042 (2)	0.0355 (18)	0.0042 (18)	−0.0054 (16)	0.0018 (17)
O1	0.081 (3)	0.040 (2)	0.059 (2)	0.003 (2)	−0.015 (2)	−0.0024 (18)
O2	0.051 (2)	0.0356 (19)	0.0417 (17)	0.0018 (15)	−0.0138 (16)	−0.0037 (14)
O3	0.064 (2)	0.044 (2)	0.0417 (17)	0.0059 (18)	−0.0178 (16)	−0.0048 (16)

Geometric parameters (Å, º) top

Cu1—O3	1.857 (3)	C11—H11A	0.9300
Cu1—N2	1.874 (4)	C12—C13	1.3900
Cu1—O2	1.890 (3)	C12—H12A	0.9300
Cu1—N3	1.963 (4)	C13—H13A	0.9300
C1—C2	1.357 (7)	C14—O3	1.276 (5)
C1—C6	1.373 (7)	C14—C15	1.328 (7)
C1—C7	1.457 (7)	C15—C16	1.394 (7)
C2—C3	1.355 (7)	C15—H15	0.9300
C2—H2	0.9300	C16—N2	1.278 (6)
C3—C4	1.369 (9)	C16—C17	1.462 (7)
C3—H3	0.9300	C17—H17A	0.9600
C4—C5	1.327 (8)	C17—H17B	0.9600
C4—H4	0.9300	C17—H17C	0.9600
C5—C6	1.367 (7)	C18—N3	1.300 (6)
C5—H5	0.9300	C18—C19	1.332 (8)
C6—O1	1.314 (6)	C18—H18	0.9300
C7—O2	1.247 (5)	C19—C20	1.323 (8)
C7—N1	1.291 (6)	C19—H19	0.9300
C8—C9	1.3900	C20—C21	1.335 (9)
C8—C13	1.3900	C20—H20	0.9300
C8—C14	1.453 (5)	C21—C22	1.356 (7)
C9—C10	1.3900	C21—H21	0.9300
C9—H9A	0.9300	C22—N3	1.300 (6)
C10—C11	1.3900	C22—H22	0.9300
C10—H10A	0.9300	N1—N2	1.355 (5)
C11—C12	1.3900	O1—H1	0.8200

O3—Cu1—N2	93.64 (15)	C12—C13—H13A	120.0
O3—Cu1—O2	173.85 (15)	C8—C13—H13A	120.0
N2—Cu1—O2	82.05 (14)	O3—C14—C15	125.4 (4)
O3—Cu1—N3	92.39 (15)	O3—C14—C8	114.0 (4)
N2—Cu1—N3	172.50 (15)	C15—C14—C8	120.6 (4)
O2—Cu1—N3	92.27 (14)	C14—C15—C16	127.5 (4)
C2—C1—C6	118.3 (5)	C14—C15—H15	116.2
C2—C1—C7	119.5 (5)	C16—C15—H15	116.2
C6—C1—C7	122.1 (5)	N2—C16—C15	119.6 (4)
C3—C2—C1	121.6 (5)	N2—C16—C17	121.5 (4)
C3—C2—H2	119.2	C15—C16—C17	118.9 (4)
C1—C2—H2	119.2	C16—C17—H17A	109.5
C2—C3—C4	119.4 (5)	C16—C17—H17B	109.5
C2—C3—H3	120.3	H17A—C17—H17B	109.5
C4—C3—H3	120.3	C16—C17—H17C	109.5
C5—C4—C3	119.5 (5)	H17A—C17—H17C	109.5
C5—C4—H4	120.2	H17B—C17—H17C	109.5
C3—C4—H4	120.2	N3—C18—C19	123.4 (5)
C4—C5—C6	121.7 (5)	N3—C18—H18	118.3
C4—C5—H5	119.2	C19—C18—H18	118.3
C6—C5—H5	119.2	C20—C19—C18	119.9 (6)
O1—C6—C5	117.5 (5)	C20—C19—H19	120.0
O1—C6—C1	123.1 (5)	C18—C19—H19	120.0
C5—C6—C1	119.4 (5)	C19—C20—C21	118.3 (6)
O2—C7—N1	124.5 (4)	C19—C20—H20	120.9
O2—C7—C1	119.7 (4)	C21—C20—H20	120.9
N1—C7—C1	115.7 (4)	C20—C21—C22	118.9 (6)
C9—C8—C13	120.0	C20—C21—H21	120.6
C9—C8—C14	119.3 (3)	C22—C21—H21	120.6
C13—C8—C14	120.6 (3)	N3—C22—C21	122.9 (5)
C10—C9—C8	120.0	N3—C22—H22	118.5
C10—C9—H9A	120.0	C21—C22—H22	118.5
C8—C9—H9A	120.0	C7—N1—N2	109.9 (4)
C9—C10—C11	120.0	C16—N2—N1	117.8 (4)
C9—C10—H10A	120.0	C16—N2—Cu1	128.6 (3)
C11—C10—H10A	120.0	N1—N2—Cu1	113.6 (3)
C12—C11—C10	120.0	C22—N3—C18	116.6 (4)
C12—C11—H11A	120.0	C22—N3—Cu1	122.0 (3)
C10—C11—H11A	120.0	C18—N3—Cu1	121.2 (4)
C11—C12—C13	120.0	C6—O1—H1	109.5
C11—C12—H12A	120.0	C7—O2—Cu1	109.9 (3)
C13—C12—H12A	120.0	C14—O3—Cu1	125.2 (3)
C12—C13—C8	120.0

C6—C1—C2—C3	0.2 (8)	N3—C18—C19—C20	1.4 (10)
C7—C1—C2—C3	−179.5 (5)	C18—C19—C20—C21	0.5 (12)
C1—C2—C3—C4	0.2 (9)	C19—C20—C21—C22	−1.4 (13)
C2—C3—C4—C5	0.1 (9)	C20—C21—C22—N3	0.3 (13)
C3—C4—C5—C6	−0.9 (10)	O2—C7—N1—N2	0.3 (6)
C4—C5—C6—O1	−178.5 (5)	C1—C7—N1—N2	180.0 (3)
C4—C5—C6—C1	1.3 (9)	C15—C16—N2—N1	−177.9 (4)
C2—C1—C6—O1	178.9 (5)	C17—C16—N2—N1	1.1 (6)
C7—C1—C6—O1	−1.5 (8)	C15—C16—N2—Cu1	1.6 (6)
C2—C1—C6—C5	−1.0 (7)	C17—C16—N2—Cu1	−179.4 (4)
C7—C1—C6—C5	178.7 (5)	C7—N1—N2—C16	177.6 (4)
C2—C1—C7—O2	2.3 (7)	C7—N1—N2—Cu1	−1.9 (4)
C6—C1—C7—O2	−177.4 (5)	O3—Cu1—N2—C16	−1.8 (4)
C2—C1—C7—N1	−177.4 (4)	O2—Cu1—N2—C16	−177.4 (4)
C6—C1—C7—N1	3.0 (7)	O3—Cu1—N2—N1	177.7 (3)
C13—C8—C9—C10	0.0	O2—Cu1—N2—N1	2.1 (3)
C14—C8—C9—C10	177.5 (4)	C21—C22—N3—C18	1.5 (10)
C8—C9—C10—C11	0.0	C21—C22—N3—Cu1	176.4 (6)
C9—C10—C11—C12	0.0	C19—C18—N3—C22	−2.4 (8)
C10—C11—C12—C13	0.0	C19—C18—N3—Cu1	−177.3 (5)
C11—C12—C13—C8	0.0	O2—Cu1—N3—C22	−175.0 (5)
C9—C8—C13—C12	0.0	O3—Cu1—N3—C18	−176.3 (4)
C14—C8—C13—C12	−177.4 (4)	O2—Cu1—N3—C18	−0.3 (4)
C9—C8—C14—O3	19.2 (5)	N1—C7—O2—Cu1	1.4 (6)
C13—C8—C14—O3	−163.4 (3)	C1—C7—O2—Cu1	−178.3 (3)
C9—C8—C14—C15	−158.8 (4)	N2—Cu1—O2—C7	−1.8 (3)
C13—C8—C14—C15	18.7 (6)	N3—Cu1—O2—C7	173.3 (4)
O3—C14—C15—C16	−1.8 (9)	C15—C14—O3—Cu1	1.0 (7)
C8—C14—C15—C16	175.9 (4)	C8—C14—O3—Cu1	−176.8 (3)
C14—C15—C16—N2	0.4 (8)	N2—Cu1—O3—C14	0.5 (4)
C14—C15—C16—C17	−178.7 (5)	N3—Cu1—O3—C14	−175.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.78	2.500 (5)	146

Experimental details

Crystal data
Chemical formula	[Cu(C₁₇H₁₄N₂O₃)(C₅H₅N)]
M_r	436.94
Crystal system, space group	Orthorhombic, C222₁
Temperature (K)	298
a, b, c (Å)	7.7096 (8), 22.906 (2), 20.983 (2)
V (Å³)	3705.6 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.28 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.728, 0.794
No. of measured, independent and observed [I > 2σ(I)] reflections	13526, 4034, 3340
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.131, 1.08
No. of reflections	4034
No. of parameters	252
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.56
Absolute structure	Flack (1983), 1761 Friedel pairs
Absolute structure parameter	0.08 (3)

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.78	2.500 (5)	146

Acknowledgements

This work was supported by the Natural Science Foundation of Anhui Provincial Education Commission (No. KJ2009A047Z)

References

Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Canpolat, E. & Kaya, M. (2004). J. Coord. Chem. 57, 1217–1223. Web of Science CrossRef CAS Google Scholar
Cozzi, P. G. (2004). Chem. Soc. Rev. 33, 410–421. Web of Science CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, X., Wu, D., Huang, X., Liu, Q., Huang, Z. & Kang, B. (1997). Polyhedron, 16, 1477–1482. CSD CrossRef CAS Web of Science Google Scholar
Singh, K., Barwa, M. S. & Tyagi, P. (2007). Eur. J. Med. Chem. 42, 394–402. Web of Science CrossRef PubMed CAS Google Scholar
Yildiz, M., Dulger, B., Koyuncu, S. Y. & Yapici, B. M. (2004). J. Indian Chem. Soc. 81, 7–12. CAS Google Scholar

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

[2-Hy­droxy-N′-(4-oxo-4-phenyl­butan-2-yl­­idene)benzohydrazidato(2−)]pyridine­copper(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

[2-Hydroxy-N′-(4-oxo-4-phenylbutan-2-ylidene)benzohydrazidato(2−)]pyridinecopper(II)