Diaqua­bis­[5-(1-oxidopyridin-1-ium-2-yl)-1,2,3,4-tetrazolido]manganese(II) di­hydrate

Gao, F.; Yao, C.-S.; Lu, Z.-S.; Shi, Y.-H.

doi:10.1107/S1600536811001620

metal-organic compounds

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Volume 67| Part 2| February 2011| Page m213

doi:10.1107/S1600536811001620

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Diaquabis[5-(1-oxidopyridin-1-ium-2-yl)-1,2,3,4-tetrazolido]manganese(II) dihydrate

Feng Gao,^a ^* Chang-Sheng Yao,^a Zai-Sheng Lu ^a and Yan-Hui Shi ^a

^aSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116 Jiangsu, People's Republic of China
^*Correspondence e-mail: gaofeng_xz2002@163.com

(Received 14 October 2010; accepted 11 January 2011; online 15 January 2011)

In the title compound, [Mn(C₆H₄N₅O)₂(H₂O)₂]·2H₂O, the Mn^II ion is situated on an inversion centre and is coordinated by the O and N atoms of two bis-chelating 5-(2-pyridyl-1-oxide)tetrazolate ligands and two O atoms of two water molecules in a distorted octahedral geometry. All the water H atoms are involved in O—H⋯N and O—H⋯O hydrogen bonds with uncoordinated water O atoms and tetrazole N atoms, which link the molecules into a three-dimensional network.

Related literature

For backgroud to tetrazolate derivatives in coordination chemistry, see: Jiang et al. (2007 ); Song et al. (2009 ); Zhang (2009). For related structures, see: Facchetti et al. (2004 ); Lin et al. (2005 ); Vrbova et al. (2000 )

Experimental

Crystal data

[Mn(C₆H₄N₅O)₂(H₂O)₂]·2H₂O
M_r = 451.29
Monoclinic, P 2₁ /c
a = 6.4808 (13) Å
b = 12.034 (2) Å
c = 12.787 (4) Å
β = 116.24 (2)°
V = 894.5 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.80 mm⁻¹
T = 293 K
0.10 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.925, T_max = 0.939
7432 measured reflections
1579 independent reflections
1102 reflections with I > 2σ(I)
R_int = 0.115

Refinement

R[F² > 2σ(F²)] = 0.078
wR(F²) = 0.133
S = 1.14
1579 reflections
133 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N2	0.88	2.15	3.010 (5)	164
O2—H2A⋯O3ⁱ	0.84	2.01	2.756 (5)	147
O2—H2B⋯N3ⁱⁱ	0.86	2.06	2.858 (5)	154
O3—H3B⋯N4ⁱⁱ	0.82	2.10	2.917 (6)	176
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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/S1600536811001620/lx2180sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001620/lx2180Isup2.hkl

checkCIF report

Comment top

Tetrazole as functional group plays an important role in coordination chemistry, medicinal chemistry and materials science applications (Song et al., 2009; Jiang et al., 2007; Zhang, 2009). It's interesting for the study of tetrazolate complexes to delineate the ways in which tetrazoles bind to metal centres. Here we report the structure of a novel substituted tetrazolato-metal complex, diaquabis(5-(2-pyridyl-1-oxide)tetrazolato)manganese(II) dihydrate.

The crystal structure of the title complex consists of the mononuclear manganese (II) unit [Mn(C₆H₄N₅O)₂(H₂O)₂], and two lattice water molecules (Fig. 1). In the mononuclear unit, manganese(II) ion is in a distorted octahedral environment, being six-coordinated by two N atoms and two O atoms from two bidentate 5-(2-pyridyl-1-oxide)tetrazolato-ligands, and two O atoms of two coordinated water molecules with Mn–O distances from 2.090 (4)Å to 2.209 (3) Å, Mn–N bond length of 2.255 (4)Å and O1–Mn1–N1 angle of 79.47 (14)°, which are comparable with the values observed in other metal-tetrazolate complexes (Vrbova et al., 2000; Lin et al., 2005; Facchetti et al., 2004). The pyridine and tetrazole rings are twisted against each other by 20.466 (190)°. In the crystal structure, all the water H atoms are involved in O–H···N and O–H···O hydrogen bonds with the solvate water O (O3W) and the tetrazole N (N2, N4) atoms. The interactions link the molecules into a three dimensional network (Table 1 and Fig. 2).

Related literature top

For backgroud to tetrazolate derivatives in coordination chemistry, see: Jiang et al. (2007); Song et al. (2009); Zhang (2009). For related structures, see: Facchetti et al. (2004); Lin et al. (2005); Vrbova et al. (2000)

Experimental top

A solution of 5-(2-pyridyl-1-oxide)tetrazole (32.6 mg, 0.2 mmol) and K₂CO₃ (13.8 mg, 0.1 mmol) in H₂O (10 ml) was dropped slowly into a solution of Mn(ClO₄).6H₂O (36.2 mg, 0.1 mmol) dissolved in methanol (10 ml). The resulting brown suspension solution was stirred for 24 h at room temperature and filtered. Yellow crystals were separated from filtrate after about one month and collected for X-ray analysis (m.p. >573 K).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Sheldrick, 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 molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) - x + 1, - y + 1, - z + 1. ]
	Fig. 2. A view of the O–H···O and O–H···N hydrogen bonds (dotted lines) in the crystal structure of the title compound.

Diaquabis[5-(1-oxidopyridin-1-ium-2-yl)-1,2,3,4-tetrazolido]manganese(II) dihydrate top

Crystal data top

[Mn(C₆H₄N₅O)₂(H₂O)₂]·2H₂O	F(000) = 462
M_r = 451.29	D_x = 1.676 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7005 reflections
a = 6.4808 (13) Å	θ = 3.1–27.6°
b = 12.034 (2) Å	µ = 0.80 mm⁻¹
c = 12.787 (4) Å	T = 293 K
β = 116.24 (2)°	Block, yellow
V = 894.5 (4) Å³	0.10 × 0.10 × 0.08 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	1579 independent reflections
Radiation source: fine-focus sealed tube	1102 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.115
Detector resolution: 10.0 pixels mm^-1	θ_max = 25.0°, θ_min = 3.4°
ϕ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −14→14
T_min = 0.925, T_max = 0.939	l = −15→15
7432 measured reflections

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)] = 0.078	Hydrogen site location: difference Fourier map
wR(F²) = 0.133	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0354P)² + 1.2794P] where P = (F_o² + 2F_c²)/3
1579 reflections	(Δ/σ)_max < 0.001
133 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Mn(C₆H₄N₅O)₂(H₂O)₂]·2H₂O	V = 894.5 (4) Å³
M_r = 451.29	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.4808 (13) Å	µ = 0.80 mm⁻¹
b = 12.034 (2) Å	T = 293 K
c = 12.787 (4) Å	0.10 × 0.10 × 0.08 mm
β = 116.24 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1579 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1102 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.939	R_int = 0.115
7432 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.14	Δρ_max = 0.39 e Å⁻³
1579 reflections	Δρ_min = −0.38 e Å⁻³
133 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
Mn1	0.5000	0.5000	0.5000	0.0282 (3)
C1	0.4458 (9)	0.2469 (4)	0.4227 (4)	0.0260 (12)
C2	0.3159 (8)	0.2280 (4)	0.4903 (4)	0.0276 (12)
C3	0.2946 (10)	0.1223 (5)	0.5282 (5)	0.0406 (15)
H3	0.3648	0.0631	0.5099	0.049*
C4	0.1752 (11)	0.1017 (6)	0.5912 (5)	0.0531 (18)
H4	0.1668	0.0303	0.6168	0.064*
C5	0.0688 (10)	0.1883 (6)	0.6155 (5)	0.0508 (17)
H2	−0.0165	0.1759	0.6568	0.061*
C6	0.0860 (9)	0.2922 (5)	0.5800 (5)	0.0407 (15)
H1	0.0140	0.3510	0.5979	0.049*
N1	0.5349 (7)	0.3443 (3)	0.4111 (3)	0.0289 (10)
N2	0.6423 (7)	0.3211 (4)	0.3443 (4)	0.0338 (11)
N3	0.6179 (8)	0.2138 (4)	0.3188 (4)	0.0368 (12)
N4	0.4943 (7)	0.1654 (4)	0.3670 (4)	0.0346 (11)
N5	0.2085 (7)	0.3114 (4)	0.5179 (4)	0.0344 (11)
O1	0.2069 (6)	0.4131 (3)	0.4819 (4)	0.0491 (11)
O2	0.2698 (6)	0.5780 (3)	0.3322 (3)	0.0396 (10)
H2A	0.1657	0.5331	0.2904	0.048*
H2B	0.2775	0.6340	0.2925	0.048*
O3	0.8363 (6)	0.4852 (3)	0.2336 (3)	0.0447 (10)
H3A	0.7951	0.4450	0.2787	0.054*
H3B	0.7388	0.5334	0.2038	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0324 (7)	0.0249 (6)	0.0313 (7)	−0.0007 (6)	0.0178 (5)	−0.0026 (6)
C1	0.028 (3)	0.024 (3)	0.025 (3)	0.001 (2)	0.011 (3)	0.002 (2)
C2	0.027 (3)	0.027 (3)	0.027 (3)	0.003 (2)	0.011 (3)	−0.005 (2)
C3	0.053 (4)	0.037 (4)	0.040 (4)	−0.001 (3)	0.028 (3)	−0.002 (3)
C4	0.069 (5)	0.050 (4)	0.046 (4)	−0.012 (4)	0.030 (4)	0.000 (3)
C5	0.046 (4)	0.069 (5)	0.038 (4)	−0.010 (4)	0.019 (3)	0.005 (4)
C6	0.033 (3)	0.061 (4)	0.035 (4)	0.005 (3)	0.021 (3)	−0.014 (3)
N1	0.030 (2)	0.033 (3)	0.026 (2)	0.000 (2)	0.016 (2)	−0.003 (2)
N2	0.032 (3)	0.041 (3)	0.032 (3)	−0.001 (2)	0.018 (2)	−0.003 (2)
N3	0.038 (3)	0.042 (3)	0.034 (3)	0.003 (2)	0.019 (2)	−0.007 (2)
N4	0.043 (3)	0.032 (3)	0.035 (3)	−0.002 (2)	0.024 (3)	−0.009 (2)
N5	0.035 (3)	0.029 (3)	0.034 (3)	0.004 (2)	0.011 (2)	0.002 (2)
O1	0.043 (3)	0.038 (2)	0.076 (3)	−0.0019 (19)	0.035 (2)	0.000 (2)
O2	0.049 (2)	0.038 (2)	0.030 (2)	−0.0062 (19)	0.016 (2)	0.0060 (18)
O3	0.046 (2)	0.040 (2)	0.055 (3)	0.005 (2)	0.028 (2)	0.012 (2)

Geometric parameters (Å, º) top

Mn1—O1	2.090 (4)	C4—H4	0.9300
Mn1—O1ⁱ	2.090 (4)	C5—C6	1.351 (8)
Mn1—O2	2.209 (3)	C5—H2	0.9300
Mn1—O2ⁱ	2.209 (3)	C6—N5	1.369 (6)
Mn1—N1	2.255 (4)	C6—H1	0.9300
Mn1—N1ⁱ	2.255 (4)	N1—N2	1.348 (5)
C1—N4	1.329 (6)	N2—N3	1.324 (6)
C1—N1	1.344 (6)	N3—N4	1.341 (6)
C1—C2	1.467 (7)	N5—O1	1.306 (5)
C2—N5	1.353 (6)	O2—H2A	0.8446
C2—C3	1.390 (7)	O2—H2B	0.8583
C3—C4	1.363 (7)	O3—H3A	0.8803
C3—H3	0.9300	O3—H3B	0.8172
C4—C5	1.359 (8)

O1—Mn1—O1ⁱ	180.0	C5—C4—C3	118.3 (6)
O1—Mn1—O2	85.11 (15)	C5—C4—H4	120.9
O1ⁱ—Mn1—O2	94.89 (14)	C3—C4—H4	120.9
O1—Mn1—O2ⁱ	94.89 (15)	C6—C5—C4	120.4 (6)
O1ⁱ—Mn1—O2ⁱ	85.11 (14)	C6—C5—H2	119.8
O2—Mn1—O2ⁱ	180.000 (1)	C4—C5—H2	119.8
O1—Mn1—N1	79.47 (14)	C5—C6—N5	120.4 (5)
O1ⁱ—Mn1—N1	100.53 (14)	C5—C6—H1	119.8
O2—Mn1—N1	92.20 (14)	N5—C6—H1	119.8
O2ⁱ—Mn1—N1	87.80 (14)	C1—N1—N2	104.9 (4)
O1—Mn1—N1ⁱ	100.53 (14)	C1—N1—Mn1	121.7 (3)
O1ⁱ—Mn1—N1ⁱ	79.47 (14)	N2—N1—Mn1	133.4 (3)
O2—Mn1—N1ⁱ	87.80 (14)	N3—N2—N1	108.6 (4)
O2ⁱ—Mn1—N1ⁱ	92.20 (14)	N2—N3—N4	109.9 (4)
N1—Mn1—N1ⁱ	180.000 (1)	C1—N4—N3	104.9 (4)
N4—C1—N1	111.7 (4)	O1—N5—C2	121.8 (4)
N4—C1—C2	122.4 (4)	O1—N5—C6	116.5 (5)
N1—C1—C2	125.9 (4)	C2—N5—C6	121.6 (5)
N5—C2—C3	116.4 (5)	N5—O1—Mn1	124.4 (3)
N5—C2—C1	122.3 (5)	Mn1—O2—H2A	110.5
C3—C2—C1	121.2 (5)	Mn1—O2—H2B	135.8
C4—C3—C2	122.8 (6)	H2A—O2—H2B	111.6
C4—C3—H3	118.6	H3A—O3—H3B	107.3
C2—C3—H3	118.6

N4—C1—C2—N5	−160.1 (5)	O2ⁱ—Mn1—N1—N2	−109.1 (4)
N1—C1—C2—N5	21.7 (8)	C1—N1—N2—N3	−0.5 (5)
N4—C1—C2—C3	19.1 (8)	Mn1—N1—N2—N3	177.0 (3)
N1—C1—C2—C3	−159.1 (5)	N1—N2—N3—N4	0.4 (5)
N5—C2—C3—C4	−0.7 (8)	N1—C1—N4—N3	−0.1 (6)
C1—C2—C3—C4	180.0 (5)	C2—C1—N4—N3	−178.5 (4)
C2—C3—C4—C5	1.4 (9)	N2—N3—N4—C1	−0.2 (5)
C3—C4—C5—C6	−1.4 (9)	C3—C2—N5—O1	−176.5 (5)
C4—C5—C6—N5	0.8 (9)	C1—C2—N5—O1	2.8 (7)
N4—C1—N1—N2	0.3 (6)	C3—C2—N5—C6	0.1 (7)
C2—C1—N1—N2	178.7 (5)	C1—C2—N5—C6	179.3 (5)
N4—C1—N1—Mn1	−177.5 (3)	C5—C6—N5—O1	176.6 (5)
C2—C1—N1—Mn1	0.9 (7)	C5—C6—N5—C2	−0.1 (8)
O1—Mn1—N1—C1	−27.4 (4)	C2—N5—O1—Mn1	−50.6 (6)
O1ⁱ—Mn1—N1—C1	152.6 (4)	C6—N5—O1—Mn1	132.7 (4)
O2—Mn1—N1—C1	−112.1 (4)	O2—Mn1—O1—N5	146.5 (4)
O2ⁱ—Mn1—N1—C1	67.9 (4)	O2ⁱ—Mn1—O1—N5	−33.5 (4)
O1—Mn1—N1—N2	155.5 (4)	N1—Mn1—O1—N5	53.3 (4)
O1ⁱ—Mn1—N1—N2	−24.5 (4)	N1ⁱ—Mn1—O1—N5	−126.7 (4)
O2—Mn1—N1—N2	70.9 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N2	0.88	2.15	3.010 (5)	164
O2—H2A···O3ⁱⁱ	0.84	2.01	2.756 (5)	147
O2—H2B···N3ⁱⁱⁱ	0.86	2.06	2.858 (5)	154
O3—H3B···N4ⁱⁱⁱ	0.82	2.10	2.917 (6)	176

Symmetry codes: (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Mn(C₆H₄N₅O)₂(H₂O)₂]·2H₂O
M_r	451.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.4808 (13), 12.034 (2), 12.787 (4)
β (°)	116.24 (2)
V (Å³)	894.5 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.10 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.925, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	7432, 1579, 1102
R_int	0.115
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.133, 1.14
No. of reflections	1579
No. of parameters	133
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.38

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT (Sheldrick, 2008), 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
O3—H3A···N2	0.88	2.15	3.010 (5)	164
O2—H2A···O3ⁱ	0.84	2.01	2.756 (5)	147
O2—H2B···N3ⁱⁱ	0.86	2.06	2.858 (5)	154
O3—H3B···N4ⁱⁱ	0.82	2.10	2.917 (6)	176

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2.

Acknowledgements

This work was supported by the Natural Science Foundation of Xuzhou Normal University (grant No. 09XLA06) and the National Natural Science Foundation of China (grant No. 21071121).

References

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Volume 67| Part 2| February 2011| Page m213

doi:10.1107/S1600536811001620

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

Di­aqua­bis­­[5-(1-oxidopyridin-1-ium-2-yl)-1,2,3,4-tetrazolido]manganese(II) di­hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Diaquabis[5-(1-oxidopyridin-1-ium-2-yl)-1,2,3,4-tetrazolido]manganese(II) dihydrate