trans-Bis[acetone (2-hydroxy­benzo­yl)hydrazonato-κ2N′,O]bis­(pyridine-κN)zinc(II)

Yang, M.-X.; Lin, S.; Chen, L.-J.; Chen, X.-H.

doi:10.1107/S1600536809001949

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages m219-m220

doi:10.1107/S1600536809001949

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trans-Bis[acetone (2-hydroxybenzoyl)hydrazonato-κ²N′,O]bis(pyridine-κN)zinc(II)

Ming-Xing Yang,^a,^b Shen Lin,^a,^b ^* Li-Juan Chen ^b and Xiao-Hua Chen ^b

^aCollege of Chemistry and Materials Science, Fujian Normal University, Fuzhou, Fujian 350007, People's Republic of China, and ^bState Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, People's Republic of China
^*Correspondence e-mail: shenlin@fjnu.edu.cn

(Received 5 December 2008; accepted 15 January 2009; online 23 January 2009)

In the title compound, [Zn(C₁₀H₁₁N₂O₂)₂(C₅H₅N)₂], the Zn^II atom lies on an inversion centre, and is coordinated in a distorted octahedral geometry by two carbonyl O atoms and two imino N atoms from two anionic bidentate acetone (2-hydroxybenzoyl)hydrazone ligands and by two N atoms from two pyridine molecules. The hydroxyl group acts as a donor, forming an intramolecular O—H⋯N hydrogen bond.

Related literature

For general background, see: Bai et al. (2006 ); Gao et al. (1998 ); Grove et al. (2004 ); Liu & Gao (1998 ); Ma et al. (1989 ). For related structures, see: Chen & Liu (2004 ); Domiano et al. (1975 ); Hu et al. (2006 , 2007 ); Li et al. (2006 ); Liu et al. (1999 ); Samanta et al. (2007 ); Wen et al. (2000 ); Wu et al. (2006 ); Xiao et al. (2000 ).

Experimental

Crystal data

[Zn(C₁₀H₁₁N₂O₂)₂(C₅H₅N)₂]
M_r = 605.99
Monoclinic, P 2₁ /n
a = 7.8225 (8) Å
b = 10.0381 (10) Å
c = 18.8201 (18) Å
β = 96.21 (4)°
V = 1469.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.88 mm⁻¹
T = 293 (2) K
0.35 × 0.26 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: none
13028 measured reflections
3282 independent reflections
2334 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.097
S = 0.98
3282 reflections
188 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O2	2.0319 (14)
Zn1—N2	2.1912 (16)
Zn1—N3	2.3013 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.99	1.61	2.535 (2)	154

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; 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/S1600536809001949/hy2173sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001949/hy2173Isup2.hkl

checkCIF report

Comment top

Hydrazones have been attracting much attention by chemists in recent years because of their biological activities, chemical and industrial versatility, and strong tendency to chelate transition metals (Bai et al., 2006; Grove et al., 2004), lanthanide metals (Ma et al., 1989) and main group metals (Gao et al., 1998; Liu & Gao, 1998). In particular, salicyloylhydrazone can be very flexible and finely tuned at the molecular level to take versatile bonding modes. It can act as a bi-, tri-, tetra- and even pentadentate ligand. A number of zinc(II) complexes with salicyloylhydrazone ligands have been studied (Hu et al., 2006; Hu et al., 2007; Li et al., 2006; Samanta et al., 2007; Wu et al., 2006). As an extension of the work on the structural characterization of salicyloylhydrazone complexes, the preparation and crystal structure of the title zinc(II) complex are reported here.

The molecular structure of the title compound is shown in Fig. 1. The Zn^II atom lies on an inversion centre and has an axially elongated octahedral coordination geometry. The two carbonyl O atoms and the two imino N atoms make up the equatorial plane and the two N atoms of two pyridine molecules occupy the axial positions at longer distances (Table 1). Double-bond character is present in C7—N1 and C8—N2, as judged from their bond lengths [1.322 (2) and 1.286 (2) Å] (Domiano et al., 1975; Liu et al., 1999; Xiao et al., 2000). The C7—O2 bond length of 1.273 (2) Å approaches the value of 1.263 Å expected for an enolic form of the hydrazone ligand (Chen & Liu, 2004; Wen et al., 2000). The data suggest enolization and deprotonation of the hydrazone groups, which is different from the analogous Zn^II complex with the same ligand (Li et al., 2006). There exists an intramolecular O—H···N hydrogen bond (Table 2).

Related literature top

For general background, see: Bai et al. (2006); Gao et al. (1998); Grove et al. (2004); Liu & Gao (1998); Ma et al. (1989). For related structures, see: Chen & Liu (2004); Domiano et al. (1975); Hu et al. (2006, 2007); Li et al. (2006); Liu et al. (1999); Samanta et al. (2007); Wen et al. (2000); Wu et al. (2006); Xiao et al. (2000).

Experimental top

All reagents were commercially available and of analytical grade. To a solution of Zn(CH₃COO)₂.2H₂O (0.110 g, 0.5 mmol) in pyridine (5 ml) was slowly added a suspension of acetone-N-salicyloylhydrazone (0.192 g, 1.0 mmol) in DMF(5 ml). The resulting red solution was stirred for 20 min and then filtered. After standing for 5 d, yellow crystals were separated from the filtrate.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); 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. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines. [Symmetry code: (i) 1 - x, -y, -z.]

trans-Bis[acetone (2-hydroxybenzoyl)hydrazonato-κ²N',O]bis(pyridine- κN)zinc(II) top

Crystal data top

[Zn(C₁₀H₁₁N₂O₂)₂(C₅H₅N)₂]	F(000) = 632
M_r = 605.99	D_x = 1.370 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3282 reflections
a = 7.8225 (8) Å	θ = 2.3–27.5°
b = 10.0381 (10) Å	µ = 0.88 mm⁻¹
c = 18.8201 (18) Å	T = 293 K
β = 96.21 (4)°	Block, yellow
V = 1469.1 (3) Å³	0.35 × 0.26 × 0.15 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID diffractometer	2334 reflections with I > 2σ(I)
Radiation source: 18 kW rotation anode	R_int = 0.034
Graphite monochromator	θ_max = 27.5°, θ_min = 2.3°
ω scans	h = 0→10
13028 measured reflections	k = 0→13
3282 independent reflections	l = −24→24

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.058P)²] where P = (F_o² + 2F_c²)/3
3282 reflections	(Δ/σ)_max < 0.001
188 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Zn(C₁₀H₁₁N₂O₂)₂(C₅H₅N)₂]	V = 1469.1 (3) Å³
M_r = 605.99	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8225 (8) Å	µ = 0.88 mm⁻¹
b = 10.0381 (10) Å	T = 293 K
c = 18.8201 (18) Å	0.35 × 0.26 × 0.15 mm
β = 96.21 (4)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2334 reflections with I > 2σ(I)
13028 measured reflections	R_int = 0.034
3282 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 0.98	Δρ_max = 0.38 e Å⁻³
3282 reflections	Δρ_min = −0.33 e Å⁻³
188 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.5000	0.0000	0.0000	0.04214 (12)
O1	0.4610 (2)	0.49143 (15)	0.11896 (11)	0.0690 (5)
H1	0.5171	0.4215	0.0926	0.113 (11)*
O2	0.35166 (17)	0.09309 (14)	0.06705 (8)	0.0492 (3)
N1	0.5358 (2)	0.27234 (16)	0.06295 (8)	0.0423 (4)
N2	0.6294 (2)	0.19207 (16)	0.02003 (8)	0.0433 (4)
N3	0.6638 (2)	−0.09222 (17)	0.09654 (9)	0.0469 (4)
C1	0.2948 (2)	0.2914 (2)	0.12902 (10)	0.0435 (4)
C2	0.3302 (3)	0.4273 (2)	0.14421 (11)	0.0525 (5)
C3	0.2284 (4)	0.4958 (3)	0.18860 (14)	0.0694 (7)
H3A	0.2484	0.5859	0.1977	0.083*
C4	0.1004 (4)	0.4326 (3)	0.21861 (15)	0.0755 (8)
H4A	0.0372	0.4790	0.2496	0.091*
C5	0.0628 (4)	0.3007 (3)	0.20383 (15)	0.0753 (7)
H5A	−0.0267	0.2587	0.2237	0.090*
C6	0.1600 (3)	0.2321 (2)	0.15905 (12)	0.0567 (5)
H6A	0.1342	0.1433	0.1487	0.068*
C7	0.3987 (2)	0.21174 (19)	0.08292 (10)	0.0397 (4)
C8	0.7671 (3)	0.2453 (2)	0.00115 (12)	0.0511 (5)
C9	0.8255 (3)	0.3833 (2)	0.02229 (16)	0.0741 (7)
H9A	0.7457	0.4226	0.0515	0.111*
H9B	0.8308	0.4364	−0.0198	0.111*
H9C	0.9374	0.3792	0.0487	0.111*
C10	0.8761 (3)	0.1689 (3)	−0.04426 (17)	0.0835 (9)
H10A	0.8262	0.0826	−0.0543	0.125*
H10B	0.9893	0.1587	−0.0195	0.125*
H10C	0.8833	0.2159	−0.0883	0.125*
C11	0.7532 (3)	−0.0149 (2)	0.14528 (13)	0.0584 (6)
H11A	0.7448	0.0771	0.1401	0.070*
C12	0.8567 (3)	−0.0653 (3)	0.20266 (13)	0.0659 (7)
H12A	0.9172	−0.0082	0.2352	0.079*
C13	0.8699 (3)	−0.2014 (3)	0.21143 (13)	0.0647 (6)
H13A	0.9398	−0.2380	0.2496	0.078*
C14	0.7773 (3)	−0.2813 (2)	0.16238 (13)	0.0624 (6)
H14A	0.7824	−0.3735	0.1667	0.075*
C15	0.6764 (3)	−0.2228 (2)	0.10655 (12)	0.0549 (5)
H15A	0.6134	−0.2781	0.0739	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.04131 (17)	0.03917 (18)	0.04726 (19)	−0.01003 (14)	0.01086 (12)	−0.00788 (15)
O1	0.0754 (11)	0.0435 (8)	0.0881 (12)	−0.0109 (8)	0.0086 (10)	−0.0158 (9)
O2	0.0496 (7)	0.0406 (7)	0.0606 (9)	−0.0129 (6)	0.0201 (6)	−0.0087 (7)
N1	0.0429 (8)	0.0400 (8)	0.0437 (8)	−0.0079 (7)	0.0031 (7)	−0.0041 (7)
N2	0.0410 (8)	0.0441 (9)	0.0447 (9)	−0.0106 (7)	0.0046 (7)	−0.0030 (7)
N3	0.0466 (9)	0.0486 (10)	0.0449 (9)	−0.0068 (8)	0.0024 (7)	−0.0018 (8)
C1	0.0495 (10)	0.0437 (10)	0.0360 (9)	0.0032 (9)	−0.0008 (8)	−0.0007 (8)
C2	0.0589 (12)	0.0486 (12)	0.0476 (12)	0.0048 (11)	−0.0056 (10)	−0.0054 (10)
C3	0.0841 (17)	0.0553 (14)	0.0669 (15)	0.0167 (14)	−0.0013 (13)	−0.0165 (13)
C4	0.0821 (18)	0.0784 (19)	0.0683 (16)	0.0286 (16)	0.0177 (14)	−0.0098 (14)
C5	0.0811 (17)	0.0750 (18)	0.0756 (17)	0.0154 (15)	0.0344 (14)	0.0028 (14)
C6	0.0617 (13)	0.0532 (13)	0.0582 (13)	0.0043 (11)	0.0201 (10)	0.0016 (11)
C7	0.0435 (9)	0.0391 (9)	0.0355 (9)	−0.0050 (8)	−0.0003 (7)	−0.0001 (8)
C8	0.0447 (10)	0.0505 (12)	0.0587 (12)	−0.0168 (9)	0.0076 (9)	0.0020 (10)
C9	0.0645 (14)	0.0572 (15)	0.102 (2)	−0.0289 (12)	0.0137 (14)	0.0001 (14)
C10	0.0660 (15)	0.0813 (19)	0.111 (2)	−0.0259 (14)	0.0433 (15)	−0.0134 (17)
C11	0.0641 (13)	0.0516 (13)	0.0571 (13)	−0.0078 (11)	−0.0041 (11)	−0.0051 (10)
C12	0.0678 (15)	0.0684 (16)	0.0573 (14)	−0.0087 (13)	−0.0130 (12)	−0.0074 (12)
C13	0.0652 (14)	0.0717 (16)	0.0536 (13)	−0.0039 (13)	−0.0107 (11)	0.0098 (12)
C14	0.0699 (15)	0.0526 (13)	0.0626 (14)	−0.0059 (12)	−0.0032 (12)	0.0078 (12)
C15	0.0588 (12)	0.0526 (12)	0.0511 (12)	−0.0104 (11)	−0.0039 (10)	−0.0007 (10)

Geometric parameters (Å, º) top

Zn1—O2ⁱ	2.0319 (14)	C4—H4A	0.9300
Zn1—O2	2.0319 (14)	C5—C6	1.379 (3)
Zn1—N2	2.1912 (16)	C5—H5A	0.9300
Zn1—N2ⁱ	2.1912 (16)	C6—H6A	0.9300
Zn1—N3ⁱ	2.3013 (18)	C8—C10	1.485 (3)
Zn1—N3	2.3013 (18)	C8—C9	1.498 (3)
O1—C2	1.338 (3)	C9—H9A	0.9600
O1—H1	0.99	C9—H9B	0.9600
O2—C7	1.273 (2)	C9—H9C	0.9600
N1—C7	1.322 (2)	C10—H10A	0.9600
N1—N2	1.402 (2)	C10—H10B	0.9600
N2—C8	1.286 (2)	C10—H10C	0.9600
N3—C15	1.326 (3)	C11—C12	1.374 (3)
N3—C11	1.339 (3)	C11—H11A	0.9300
C1—C6	1.384 (3)	C12—C13	1.379 (4)
C1—C2	1.415 (3)	C12—H12A	0.9300
C1—C7	1.485 (3)	C13—C14	1.369 (3)
C2—C3	1.396 (3)	C13—H13A	0.9300
C3—C4	1.359 (4)	C14—C15	1.375 (3)
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.378 (4)	C15—H15A	0.9300

O2ⁱ—Zn1—O2	180.00 (6)	C6—C5—H5A	120.5
O2ⁱ—Zn1—N2	103.14 (6)	C5—C6—C1	122.0 (2)
O2—Zn1—N2	76.86 (6)	C5—C6—H6A	119.0
O2ⁱ—Zn1—N2ⁱ	76.86 (6)	C1—C6—H6A	119.0
O2—Zn1—N2ⁱ	103.14 (6)	O2—C7—N1	125.93 (18)
N2—Zn1—N2ⁱ	180.00 (9)	O2—C7—C1	118.57 (17)
O2ⁱ—Zn1—N3ⁱ	90.07 (6)	N1—C7—C1	115.49 (17)
O2—Zn1—N3ⁱ	89.93 (6)	N2—C8—C10	119.64 (19)
N2—Zn1—N3ⁱ	89.38 (6)	N2—C8—C9	123.4 (2)
N2ⁱ—Zn1—N3ⁱ	90.62 (6)	C10—C8—C9	116.92 (19)
O2ⁱ—Zn1—N3	89.93 (6)	C8—C9—H9A	109.5
O2—Zn1—N3	90.07 (6)	C8—C9—H9B	109.5
N2—Zn1—N3	90.62 (6)	H9A—C9—H9B	109.5
N2ⁱ—Zn1—N3	89.38 (6)	C8—C9—H9C	109.5
N3ⁱ—Zn1—N3	180.00 (10)	H9A—C9—H9C	109.5
C2—O1—H1	103.6	H9B—C9—H9C	109.5
C7—O2—Zn1	113.95 (12)	C8—C10—H10A	109.5
C7—N1—N2	112.91 (15)	C8—C10—H10B	109.5
C8—N2—N1	115.16 (17)	H10A—C10—H10B	109.5
C8—N2—Zn1	134.68 (15)	C8—C10—H10C	109.5
N1—N2—Zn1	110.16 (11)	H10A—C10—H10C	109.5
C15—N3—C11	116.73 (19)	H10B—C10—H10C	109.5
C15—N3—Zn1	122.43 (14)	N3—C11—C12	123.0 (2)
C11—N3—Zn1	120.83 (15)	N3—C11—H11A	118.5
C6—C1—C2	118.3 (2)	C12—C11—H11A	118.5
C6—C1—C7	119.76 (18)	C11—C12—C13	119.3 (2)
C2—C1—C7	121.98 (19)	C11—C12—H12A	120.4
O1—C2—C3	118.9 (2)	C13—C12—H12A	120.4
O1—C2—C1	122.2 (2)	C14—C13—C12	118.2 (2)
C3—C2—C1	119.0 (2)	C14—C13—H13A	120.9
C4—C3—C2	120.8 (2)	C12—C13—H13A	120.9
C4—C3—H3A	119.6	C13—C14—C15	118.9 (2)
C2—C3—H3A	119.6	C13—C14—H14A	120.6
C3—C4—C5	121.0 (3)	C15—C14—H14A	120.6
C3—C4—H4A	119.5	N3—C15—C14	123.9 (2)
C5—C4—H4A	119.5	N3—C15—H15A	118.0
C4—C5—C6	118.9 (3)	C14—C15—H15A	118.0
C4—C5—H5A	120.5

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.99	1.61	2.535 (2)	154

Experimental details

Crystal data
Chemical formula	[Zn(C₁₀H₁₁N₂O₂)₂(C₅H₅N)₂]
M_r	605.99
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.8225 (8), 10.0381 (10), 18.8201 (18)
β (°)	96.21 (4)
V (Å³)	1469.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	0.35 × 0.26 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13028, 3282, 2334
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.097, 0.98
No. of reflections	3282
No. of parameters	188
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.33

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O2	2.0319 (14)	Zn1—N3	2.3013 (18)
Zn1—N2	2.1912 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.99	1.61	2.535 (2)	154

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 20771024), the Natural Science Foundation of Fujian Province (grant No. 2008 J0142) and the Foundation of the State Key Laboratory of Structural Chemistry (grant No. 070032).

References

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