Aqua­bis(3′-hydr­oxy-2,2′-bipyridine-3-olato-κ2N,N′)zinc(II)

Zhang, S.G.; Hou, C.

doi:10.1107/S1600536808024495

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1131

doi:10.1107/S1600536808024495

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Aquabis(3′-hydroxy-2,2′-bipyridine-3-olato-κ²N,N′)zinc(II)

Shi Guo Zhang ^a ^* and Chao Hou ^b

^aDepartment of Chemistry and Chemical Engineering, Institute of Materials Chemistry, Binzhou University, Binzhou 256603, People's Republic of China, and ^bDepartment of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China
^*Correspondence e-mail: zhangshiguo1970@yahoo.com.cn

(Received 25 May 2008; accepted 31 July 2008; online 6 August 2008)

In the title complex, [Zn(C₁₀H₇N₂O₂)₂(H₂O)], the Zn^II ion and water O atom are located on a crystallographic twofold rotation axis and the metal atom assumes a distorted trigonal-bipyramidal ZnN₄O coordination geometry. An intramolecular O—H⋯O hydrogen bond occurs within the ligand and intermolecular O—H⋯O hydrogen bonds involving the water molecule result in a sheet structure in the crystal structure. In addition, a short C—O⋯π contact between the O atom of the deprotonated hydroxyl group and a nearby pyridine ring [O⋯Cg = 3.977 (2) Å, where Cg is the centroid of the pyridine ring] is observed.

Related literature

For related structures, see: Cargill Thompson et al. (1996 ); Stephenson & Hardie (2007 ).

Experimental

Crystal data

[Zn(C₁₀H₇N₂O₂)₂(H₂O)]
M_r = 457.74
Orthorhombic, P b c n
a = 13.931 (2) Å
b = 9.1685 (16) Å
c = 14.364 (3) Å
V = 1834.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.38 mm⁻¹
T = 298 (2) K
0.40 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.608, T_max = 0.770
8883 measured reflections
1621 independent reflections
1293 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.083
S = 1.05
1621 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—N1	2.081 (2)
Zn1—N2	2.0716 (18)
O3—Zn1	2.002 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H5⋯O2	0.82	1.61	2.410 (3)	165
O3—H1⋯O2ⁱ	0.80	1.83	2.630 (2)	174
Symmetry code: (i) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024495/hb2736sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808024495/hb2736Isup2.hkl

checkCIF report

Comment top

2,2'-Bipyridine-3,3'-diol (bpd) has the potential to be a useful multi-dentate ligand and may act as a bridging ligand due to coordination of its N and O atoms. A few multi-nuclear complexes have been synthesized with mono-deprotonated bpd as a bridging ligand (Cargill Thompson et al. 1996; Stephenson & Hardie, 2007). We attempted to prepare a similar compound, but instead we obtained the mono-nuclear title complex, (I), (Fig. 1) and report its structure herein.

The Zn1 atom in (I) lies in a twofold axis and is in a distorted trigonal bipyramidal geometry (Table 1). The dihedral angle between the N1 and N2 ring mean planes is 13.08 (12)°. An intramolecular O—H···O hydrogen bond between O atom of deprotonated hydroxyl and hydroxyl group (Table 2) occcurs within the ligand. The water molecule (O atom site symmetry 2) makes an intermolecular O—H···.O hydrogen bond to result in a supramolecular sheet structure in the ab plane (Fig. 2). In addition to the hydrogen bonds there is weak interaction between C—O bond and pyridine ring and the relevant distances are as follows: C4—O2···Cg1ⁱ = 3.977 (2) Å and C4—O2···Cg1ⁱ_perp = 3.635 Å [Cg1 is the centroid of N1/C1—C5 ring, C4—O2···Cg1ⁱ_perp is the perpendicular distance from O2 atom to ring Cg1ⁱ; symmetry code: (i) 1/2-x, 1/2+y, z].

Related literature top

For related structure, see: Cargill Thompson et al. (1996); Stephenson & Hardie (2007).

Experimental top

A 10-ml H₂O solution of ZnCl₂ (0.1214 g, 0.891 mmol) was added to a 10-ml hot ethanol solution containing 2,2'-bipyridine-3,3'-diol (0.1664 g, 0.884 mmol), and the mixed solution was stirred for a few minutes. Yellow blocks of (I) were obtained after the solution had been allowed to stand at room temperature for two weeks.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

	Fig. 1. View of (I), showing displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level. The hydrogen bond is indicated by a dashed line. Symmetry code: (i) -1/2 + x, -1/2 + y, 3/2 - z
	Fig. 2. Intermolecular hydrogen bonds (dashed line) in the crystal of (I).

Aquabis(3'-hydroxy-2,2'-bipyridine-3-olato-κ²N,N')zinc(II) top

Crystal data top

[Zn(C₁₀H₇N₂O₂)₂(H₂O)]	F(000) = 936
M_r = 457.74	D_x = 1.657 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2299 reflections
a = 13.931 (2) Å	θ = 2.7–24.6°
b = 9.1685 (16) Å	µ = 1.38 mm⁻¹
c = 14.364 (3) Å	T = 298 K
V = 1834.7 (6) Å³	Block, yellow
Z = 4	0.40 × 0.21 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	1621 independent reflections
Radiation source: fine-focus sealed tube	1293 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −15→16
T_min = 0.608, T_max = 0.770	k = −9→10
8883 measured reflections	l = −17→17

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)] = 0.030	Hydrogen site location: difmap and geom
wR(F²) = 0.083	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0435P)² + 0.4048P] where P = (F_o² + 2F_c²)/3
1621 reflections	(Δ/σ)_max < 0.001
137 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[Zn(C₁₀H₇N₂O₂)₂(H₂O)]	V = 1834.7 (6) Å³
M_r = 457.74	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 13.931 (2) Å	µ = 1.38 mm⁻¹
b = 9.1685 (16) Å	T = 298 K
c = 14.364 (3) Å	0.40 × 0.21 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	1621 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1293 reflections with I > 2σ(I)
T_min = 0.608, T_max = 0.770	R_int = 0.035
8883 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
1621 reflections	Δρ_min = −0.22 e Å⁻³
137 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
C1	0.18495 (17)	−0.0831 (3)	0.84200 (18)	0.0497 (6)
H8A	0.1443	−0.1318	0.8829	0.060*
C2	0.28226 (18)	−0.0979 (3)	0.85235 (18)	0.0505 (6)
H7	0.3078	−0.1560	0.8993	0.061*
C3	0.34041 (17)	−0.0251 (3)	0.7919 (2)	0.0484 (6)
H6A	0.4066	−0.0346	0.7980	0.058*
C4	0.30414 (16)	0.0627 (3)	0.72164 (17)	0.0405 (6)
C5	0.20250 (14)	0.0718 (2)	0.71420 (15)	0.0328 (5)
C6	0.14629 (15)	0.1528 (2)	0.64177 (14)	0.0335 (5)
C7	0.18121 (17)	0.2589 (3)	0.57966 (15)	0.0433 (6)
C8	0.1158 (2)	0.3273 (3)	0.52075 (16)	0.0532 (7)
H4	0.1371	0.4013	0.4816	0.064*
C9	0.0216 (2)	0.2884 (3)	0.51908 (18)	0.0530 (7)
H3	−0.0212	0.3329	0.4783	0.064*
C10	−0.00846 (16)	0.1818 (3)	0.57930 (17)	0.0482 (6)
H2	−0.0724	0.1528	0.5782	0.058*
N1	0.14707 (14)	−0.00122 (19)	0.77522 (15)	0.0401 (5)
N2	0.05150 (12)	0.11824 (19)	0.63953 (12)	0.0379 (5)
O1	0.27183 (13)	0.3017 (2)	0.57387 (13)	0.0673 (6)
H5	0.3044	0.2553	0.6111	0.101*
O2	0.36348 (11)	0.1306 (2)	0.66513 (12)	0.0574 (5)
O3	0.0000	−0.2225 (3)	0.7500	0.0640 (8)
H1	−0.0443	−0.2657	0.7730	0.096*
Zn1	0.0000	−0.00413 (4)	0.7500	0.03787 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0382 (14)	0.0538 (16)	0.0571 (16)	−0.0007 (11)	−0.0022 (12)	0.0162 (12)
C2	0.0420 (14)	0.0485 (15)	0.0610 (16)	0.0054 (11)	−0.0147 (12)	0.0037 (12)
C3	0.0248 (12)	0.0561 (16)	0.0644 (16)	0.0022 (11)	−0.0092 (13)	−0.0119 (13)
C4	0.0291 (12)	0.0451 (13)	0.0474 (13)	−0.0045 (11)	0.0016 (11)	−0.0133 (11)
C5	0.0264 (11)	0.0330 (12)	0.0389 (12)	−0.0026 (9)	0.0007 (9)	−0.0086 (10)
C6	0.0311 (12)	0.0340 (11)	0.0353 (11)	0.0003 (9)	0.0039 (9)	−0.0069 (9)
C7	0.0451 (14)	0.0455 (14)	0.0393 (13)	−0.0082 (11)	0.0066 (11)	−0.0059 (11)
C8	0.0669 (19)	0.0496 (16)	0.0432 (14)	−0.0014 (13)	0.0054 (13)	0.0075 (12)
C9	0.0555 (16)	0.0570 (17)	0.0464 (15)	0.0136 (14)	−0.0026 (12)	0.0049 (13)
C10	0.0356 (14)	0.0567 (16)	0.0525 (15)	0.0114 (11)	−0.0028 (11)	0.0013 (13)
N1	0.0276 (11)	0.0446 (12)	0.0482 (11)	0.0002 (8)	0.0001 (9)	0.0067 (9)
N2	0.0272 (10)	0.0421 (11)	0.0444 (11)	0.0025 (8)	0.0014 (8)	0.0001 (8)
O1	0.0538 (12)	0.0821 (14)	0.0661 (12)	−0.0260 (10)	0.0022 (9)	0.0184 (11)
O2	0.0277 (9)	0.0776 (13)	0.0669 (11)	−0.0141 (8)	0.0075 (8)	−0.0009 (10)
O3	0.0353 (14)	0.0391 (14)	0.118 (2)	0.000	0.0278 (13)	0.000
Zn1	0.0232 (2)	0.0418 (3)	0.0487 (3)	0.000	0.00383 (15)	0.000

Geometric parameters (Å, º) top

C1—N1	1.328 (3)	C7—C8	1.392 (3)
C1—C2	1.370 (3)	C8—C9	1.361 (4)
C1—H8A	0.9300	C8—H4	0.9300
C2—C3	1.362 (4)	C9—C10	1.371 (4)
C2—H7	0.9300	C9—H3	0.9300
C3—C4	1.386 (4)	C10—N2	1.336 (3)
C3—H6A	0.9300	C10—H2	0.9300
C4—O2	1.315 (3)	O1—H5	0.8200
C4—C5	1.422 (3)	O3—H1	0.8042
C5—N1	1.346 (3)	Zn1—N1	2.081 (2)
C5—C6	1.499 (3)	Zn1—N2	2.0716 (18)
C6—N2	1.359 (3)	Zn1—N2ⁱ	2.0716 (18)
C6—C7	1.407 (3)	Zn1—N1ⁱ	2.081 (2)
C7—O1	1.324 (3)	O3—Zn1	2.002 (2)

N1—C1—C2	121.8 (2)	C8—C9—C10	118.0 (2)
N1—C1—H8A	119.1	C8—C9—H3	121.0
C2—C1—H8A	119.1	C10—C9—H3	121.0
C3—C2—C1	118.1 (2)	N2—C10—C9	121.9 (2)
C3—C2—H7	121.0	N2—C10—H2	119.0
C1—C2—H7	121.0	C9—C10—H2	119.0
C2—C3—C4	122.1 (2)	C1—N1—C5	121.6 (2)
C2—C3—H6A	118.9	C1—N1—Zn1	120.67 (16)
C4—C3—H6A	118.9	C5—N1—Zn1	117.24 (15)
O2—C4—C3	119.7 (2)	C10—N2—C6	121.4 (2)
O2—C4—C5	123.5 (2)	C10—N2—Zn1	121.03 (15)
C3—C4—C5	116.8 (2)	C6—N2—Zn1	116.41 (14)
N1—C5—C4	119.5 (2)	C7—O1—H5	109.5
N1—C5—C6	113.49 (18)	Zn1—O3—H1	119.5
C4—C5—C6	126.9 (2)	O3—Zn1—N2	122.79 (5)
N2—C6—C7	118.8 (2)	O3—Zn1—N2ⁱ	122.79 (5)
N2—C6—C5	114.11 (18)	N2—Zn1—N2ⁱ	114.42 (10)
C7—C6—C5	127.03 (19)	O3—Zn1—N1	90.73 (5)
O1—C7—C8	116.9 (2)	N2—Zn1—N1	77.61 (7)
O1—C7—C6	125.0 (2)	N2ⁱ—Zn1—N1	101.58 (7)
C8—C7—C6	118.1 (2)	O3—Zn1—N1ⁱ	90.73 (5)
C9—C8—C7	121.6 (2)	N2—Zn1—N1ⁱ	101.58 (7)
C9—C8—H4	119.2	N2ⁱ—Zn1—N1ⁱ	77.61 (7)
C7—C8—H4	119.2	N1—Zn1—N1ⁱ	178.53 (10)

N1—C1—C2—C3	0.3 (4)	C4—C5—N1—Zn1	−172.45 (15)
C1—C2—C3—C4	0.3 (4)	C6—C5—N1—Zn1	5.8 (2)
C2—C3—C4—O2	−180.0 (2)	C9—C10—N2—C6	−2.3 (4)
C2—C3—C4—C5	−1.0 (4)	C9—C10—N2—Zn1	165.07 (19)
O2—C4—C5—N1	−179.9 (2)	C7—C6—N2—C10	0.6 (3)
C3—C4—C5—N1	1.2 (3)	C5—C6—N2—C10	179.53 (19)
O2—C4—C5—C6	2.1 (4)	C7—C6—N2—Zn1	−167.35 (15)
C3—C4—C5—C6	−176.8 (2)	C5—C6—N2—Zn1	11.6 (2)
N1—C5—C6—N2	−11.3 (3)	C10—N2—Zn1—O3	102.57 (17)
C4—C5—C6—N2	166.8 (2)	C6—N2—Zn1—O3	−89.42 (15)
N1—C5—C6—C7	167.5 (2)	C10—N2—Zn1—N2ⁱ	−77.43 (17)
C4—C5—C6—C7	−14.4 (3)	C6—N2—Zn1—N2ⁱ	90.58 (15)
N2—C6—C7—O1	−179.3 (2)	C10—N2—Zn1—N1	−174.67 (19)
C5—C6—C7—O1	1.9 (4)	C6—N2—Zn1—N1	−6.65 (14)
N2—C6—C7—C8	2.2 (3)	C10—N2—Zn1—N1ⁱ	4.08 (19)
C5—C6—C7—C8	−176.6 (2)	C6—N2—Zn1—N1ⁱ	172.10 (14)
O1—C7—C8—C9	178.0 (2)	C1—N1—Zn1—O3	−48.31 (19)
C6—C7—C8—C9	−3.4 (4)	C5—N1—Zn1—O3	123.54 (16)
C7—C8—C9—C10	1.8 (4)	C1—N1—Zn1—N2	−171.8 (2)
C8—C9—C10—N2	1.1 (4)	C5—N1—Zn1—N2	0.05 (16)
C2—C1—N1—C5	−0.1 (4)	C1—N1—Zn1—N2ⁱ	75.4 (2)
C2—C1—N1—Zn1	171.39 (19)	C5—N1—Zn1—N2ⁱ	−112.72 (16)
C4—C5—N1—C1	−0.7 (3)	C1—N1—Zn1—N1ⁱ	131.69 (18)
C6—C5—N1—C1	177.6 (2)	C5—N1—Zn1—N1ⁱ	−56.46 (16)

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H5···O2	0.82	1.61	2.410 (3)	165
O3—H1···O2ⁱⁱ	0.80	1.83	2.630 (2)	174

Symmetry code: (ii) x−1/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₀H₇N₂O₂)₂(H₂O)]
M_r	457.74
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	13.931 (2), 9.1685 (16), 14.364 (3)
V (Å³)	1834.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.38
Crystal size (mm)	0.40 × 0.21 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.608, 0.770
No. of measured, independent and observed [I > 2σ(I)] reflections	8883, 1621, 1293
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.083, 1.05
No. of reflections	1621
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.22

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008) and local programs.

Selected bond lengths (Å) top

Zn1—N1	2.081 (2)	O3—Zn1	2.002 (2)
Zn1—N2	2.0716 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H5···O2	0.82	1.61	2.410 (3)	165
O3—H1···O2ⁱ	0.80	1.83	2.630 (2)	174

Symmetry code: (i) x−1/2, y−1/2, −z+3/2.

Acknowledgements

The authors thank the Natural Science Foundation of Shandong Province of China (Grant No. Y2007B26).

References

Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cargill Thompson, A. M. W., Jeffery, J. C., Liard, D. J. & Ward, M. D. (1996). J. Chem. Soc. Dalton Trans. pp. 879–884. CrossRef Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stephenson, M. D. & Hardie, M. J. (2007). CrystEngComm. 9, 496–502. Web of Science CSD CrossRef CAS Google Scholar