[2-Hydroxy-N'-(4-oxo-4-phenyl-butan-2-yl-idene)benzohydrazidato(2-)]pyridine-copper(II).

The mononuclear title complex, [Cu(C(17)H(14)N(2)O(3))(C(5)H(5)N)], was synthesized by the reaction of CuCl(2)·2H(2)O with N-(4-oxo-4-phenyl-butan-2-yl-idene)benzohydrazide (H(2)L). 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 intra-molecular O-H⋯N inter-action occurs.

Related literature

For the biological properties of Schiff base–n class="Chemical">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(C17n class="Species">H14N2O3)(C5H5N)]

M = 436.94

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.131

S = 1.08

4034 reflections

252 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.56 e Å−3

Absolute structure: Flack (1983 ▶), 1761 Friedel pairs

Flack parameter: 0.08 (3)

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAIn class="Chemical">NT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047719/bx2325sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047719/bx2325Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C17H14N2O3)(C5H5N)]	F(000) = 1800
Mr = 436.94	Dx = 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

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

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(Fo2) + (0.0614P)2 + 1.8583P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.003
4034 reflections	Δρmax = 0.45 e Å−3
252 parameters	Δρmin = −0.56 e Å−3
0 restraints	Absolute structure: Flack (1983), 1761 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (3)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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