catena-Poly[[[[3-(2-pyrid­yl)-1H-pyrazole]manganese(II)]-μ-oxalato] sesquihydrate]

An, Z.; Zhu, L.

doi:10.1107/S1600536809044298

metal-organic compounds

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Volume 65| Part 11| November 2009| Page m1480

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catena-Poly[[[[3-(2-pyridyl)-1H-pyrazole]manganese(II)]-μ-oxalato] sesquihydrate]

Zhe An ^a ^* and Ling Zhu ^a

^aSchool of Chemistry and Life Science, Maoming University, Maoming 525000, People's Republic of China
^*Correspondence e-mail: anz_md@163.com

(Received 20 October 2009; accepted 24 October 2009; online 31 October 2009)

In the title compound, {[Mn(C₂O₄)(C₈H₇N₃)]·1.5H₂O}_n, the Mn^II ion is chelated by two O,O′-bidentate oxalate ions and an N,N′-bidentate 3-(2-pyridyl)pyrazole molecule, resulting in a distorted cis-MnN₂O₄ octahedral geometry for the metal ion. The bridging oxalate ions generate wave-like polymeric chains propagating in [001]. The packing is consolidated by N—H⋯O and O—H⋯O hydrogen bonds. One of the water O atoms lies on a crystallographic twofold axis.

Related literature

For coordination compounds with pyridyl-pyrazolide ligands, see: Ward et al. (1998 , 2001 ).

Experimental

Crystal data

[Mn(C₂O₄)(C₈H₇N₃)]·1.5H₂O
M_r = 315.15
Monoclinic, C 2/c
a = 29.460 (8) Å
b = 9.236 (3) Å
c = 9.875 (3) Å
β = 102.706 (5)°
V = 2621.0 (13) Å³
Z = 8
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 296 K
0.43 × 0.28 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.665, T_max = 0.805
6809 measured reflections
2438 independent reflections
2004 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.078
S = 1.00
2438 reflections
186 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Mn1—N1	2.280 (4)
Mn1—N2	2.223 (4)
Mn1—O4ⁱ	2.150 (3)
Mn1—O2	2.168 (3)
Mn1—O1	2.191 (4)
Mn1—O3ⁱ	2.208 (3)

N2—Mn1—N1	73.01 (16)
Symmetry code: (i) $[x, -y, z-{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1W	0.86	1.89	2.748 (7)	175
O1W—H1W⋯O1ⁱⁱ	0.83 (5)	2.08 (4)	2.851 (6)	155 (6)
O1W—H2W⋯O2Wⁱⁱⁱ	0.82 (4)	2.10 (5)	2.819 (6)	148 (6)
O2W—H3W⋯O3^iv	0.82 (5)	2.06 (4)	2.823 (4)	156 (6)
Symmetry codes: (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z; (iv) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: SMART or APEX2? (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809044298/hb5162sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044298/hb5162Isup2.hkl

checkCIF report

Comment top

The tridentate ligand 3-(2-pyridyl)pyrazole and its derivatives have been used widely in the construction of supramolecular architectures by way of metal-organic coordination (Ward, Fleming et al. 1998; Ward, 2001).

As a continuation of these studies, we now report the crystal structure of the title complex, (I).

The Mn ion is hexcoordianted, chelated by two oxalate and one 3-(2-pyridyl)pyrazole ligand (Table 1). While each oxalate ligand acts as one bridige to chalate two Mn ions, forming one wave-like line with Mn···Mn distance being 5.652 /%A, shown in Figure 2. The structure is consolidated by N—H···O and O—H···O hydrogen bonds (Table 2, Figure 3).

Related literature top

For coordination compounds with pyridyl-pyrazolide ligands, see: Ward et al. (1998, 2001).

Experimental top

A mixture of Mn(CH₃COO)₂.4H₂O (1 mmol), 3-(2-pyridyl)pyrazole (1 mmol), oxalic acid (1 mmol), sodium hydroxide (1 mmol) and H₂O (10 ml) was stirred for 30 min in air. The mixture was then transferred to a 25 ml Teflon-lined hydrothermal bomb. The bomb was kept at 433 K for 72 h under autogenous pressure. Upon cooling, pink prisms of (I) were obtained from the reaction mixture.

Structure description top

As a continuation of these studies, we now report the crystal structure of the title complex, (I).

For coordination compounds with pyridyl-pyrazolide ligands, see: Ward et al. (1998, 2001).

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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: SHELXTL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of (I) with the unique-atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of (I) showing the extended chain strcuture.
	Fig. 3. A view of (I) showing the packing.

catena-Poly[[[[3-(2-pyridyl)-1H-pyrazole]manganese(II)]- µ-oxalato] sesquihydrate] top

Crystal data top

[Mn(C₂O₄)(C₈H₇N₃)]·1.5H₂O	F(000) = 1280
M_r = 315.15	D_x = 1.597 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2634 reflections
a = 29.460 (8) Å	θ = 2.8–25.4°
b = 9.236 (3) Å	µ = 1.03 mm⁻¹
c = 9.875 (3) Å	T = 296 K
β = 102.706 (5)°	Block, pink
V = 2621.0 (13) Å³	0.43 × 0.28 × 0.22 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	2438 independent reflections
Radiation source: fine-focus sealed tube	2004 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
φ and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −35→35
T_min = 0.665, T_max = 0.805	k = −10→11
6809 measured reflections	l = −9→11

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.045P)² + 0.7224P] where P = (F_o² + 2F_c²)/3
2438 reflections	(Δ/σ)_max = 0.001
186 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

[Mn(C₂O₄)(C₈H₇N₃)]·1.5H₂O	V = 2621.0 (13) Å³
M_r = 315.15	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 29.460 (8) Å	µ = 1.03 mm⁻¹
b = 9.236 (3) Å	T = 296 K
c = 9.875 (3) Å	0.43 × 0.28 × 0.22 mm
β = 102.706 (5)°

Data collection top

Bruker APEXII CCD diffractometer	2438 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2004 reflections with I > 2σ(I)
T_min = 0.665, T_max = 0.805	R_int = 0.020
6809 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.22 e Å⁻³
2438 reflections	Δρ_min = −0.17 e Å⁻³
186 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	0.2903 (2)	0.3204 (7)	0.3530 (6)	0.0620 (16)
H1	0.2780	0.2284	0.3594	0.074*
C2	0.2697 (2)	0.4365 (8)	0.4029 (7)	0.0732 (19)
H2	0.2441	0.4229	0.4423	0.088*
C3	0.2872 (2)	0.5721 (8)	0.3938 (7)	0.077 (2)
H3	0.2740	0.6518	0.4279	0.092*
C4	0.3246 (2)	0.5889 (7)	0.3340 (7)	0.0685 (17)
H4	0.3367	0.6806	0.3257	0.082*
C5	0.34421 (19)	0.4681 (6)	0.2858 (5)	0.0483 (13)
C6	0.3844 (2)	0.4772 (6)	0.2209 (6)	0.0506 (13)
C7	0.4082 (3)	0.5950 (7)	0.1822 (8)	0.079 (2)
H7	0.4024	0.6926	0.1940	0.095*
C8	0.4416 (3)	0.5372 (7)	0.1235 (8)	0.085 (2)
H8	0.4632	0.5886	0.0868	0.102*
C9	0.39499 (16)	0.0253 (5)	0.5065 (5)	0.0374 (11)
C10	0.34569 (16)	−0.0362 (5)	0.4432 (5)	0.0367 (11)
N1	0.32730 (15)	0.3343 (5)	0.2955 (5)	0.0472 (11)
N2	0.40299 (15)	0.3533 (4)	0.1877 (5)	0.0470 (11)
N3	0.43793 (17)	0.3939 (6)	0.1279 (5)	0.0628 (13)
H3A	0.4556	0.3346	0.0965	0.075*
Mn1	0.36805 (2)	0.14892 (8)	0.22637 (7)	0.0395 (3)
O1	0.41292 (12)	0.1050 (4)	0.4304 (4)	0.0476 (9)
O2	0.32916 (13)	−0.0076 (4)	0.3189 (4)	0.0514 (9)
O3	0.41261 (12)	−0.0083 (4)	0.6295 (3)	0.0477 (9)
O4	0.32667 (11)	−0.1102 (4)	0.5215 (3)	0.0433 (8)
O1W	0.49441 (17)	0.2150 (6)	0.0153 (6)	0.0849 (14)
O2W	0.5000	0.8860 (7)	0.2500	0.0754 (19)
H1W	0.5197 (14)	0.181 (7)	0.056 (5)	0.080*
H2W	0.485 (2)	0.183 (7)	−0.063 (4)	0.080*
H3W	0.4792 (17)	0.944 (6)	0.222 (7)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.055 (3)	0.068 (4)	0.070 (4)	0.001 (3)	0.027 (3)	−0.007 (3)
C2	0.054 (4)	0.092 (5)	0.080 (5)	0.015 (4)	0.028 (3)	−0.012 (4)
C3	0.074 (4)	0.079 (5)	0.078 (5)	0.028 (4)	0.019 (4)	−0.021 (4)
C4	0.079 (4)	0.049 (3)	0.076 (4)	0.008 (3)	0.016 (4)	−0.018 (3)
C5	0.054 (3)	0.043 (3)	0.046 (3)	0.004 (2)	0.007 (2)	−0.007 (2)
C6	0.057 (3)	0.040 (3)	0.055 (3)	−0.003 (2)	0.012 (3)	−0.002 (2)
C7	0.101 (5)	0.041 (3)	0.104 (6)	−0.009 (3)	0.039 (5)	0.007 (3)
C8	0.091 (5)	0.065 (4)	0.112 (6)	−0.022 (4)	0.047 (5)	0.013 (4)
C9	0.042 (3)	0.035 (3)	0.037 (3)	−0.002 (2)	0.013 (2)	−0.003 (2)
C10	0.043 (3)	0.032 (2)	0.038 (3)	−0.003 (2)	0.013 (2)	−0.004 (2)
N1	0.048 (2)	0.046 (3)	0.051 (3)	0.0022 (19)	0.017 (2)	−0.0065 (19)
N2	0.051 (3)	0.041 (2)	0.053 (3)	−0.0033 (19)	0.021 (2)	0.0016 (19)
N3	0.061 (3)	0.063 (3)	0.074 (3)	−0.006 (2)	0.035 (3)	0.008 (3)
Mn1	0.0490 (5)	0.0355 (5)	0.0370 (5)	0.0002 (3)	0.0160 (3)	−0.0001 (3)
O1	0.046 (2)	0.055 (2)	0.043 (2)	−0.0140 (16)	0.0116 (16)	0.0073 (16)
O2	0.056 (2)	0.059 (2)	0.037 (2)	−0.0187 (18)	0.0051 (16)	0.0048 (16)
O3	0.046 (2)	0.057 (2)	0.039 (2)	−0.0124 (16)	0.0069 (16)	0.0062 (16)
O4	0.0449 (19)	0.0467 (19)	0.0401 (19)	−0.0105 (15)	0.0132 (16)	0.0017 (15)
O1W	0.060 (3)	0.103 (4)	0.097 (4)	0.016 (3)	0.027 (3)	−0.002 (3)
O2W	0.047 (4)	0.069 (4)	0.102 (5)	0.000	−0.002 (4)	0.000

Geometric parameters (Å, º) top

C1—N1	1.342 (7)	C9—O3	1.250 (6)
C1—C2	1.376 (8)	C9—C10	1.557 (7)
C1—H1	0.9300	C10—O2	1.245 (6)
C2—C3	1.365 (10)	C10—O4	1.253 (5)
C2—H2	0.9300	N2—N3	1.348 (6)
C3—C4	1.367 (9)	N3—H3A	0.8600
C3—H3	0.9300	Mn1—N1	2.280 (4)
C4—C5	1.388 (8)	Mn1—N2	2.223 (4)
C4—H4	0.9300	Mn1—O4ⁱ	2.150 (3)
C5—N1	1.344 (6)	Mn1—O2	2.168 (3)
C5—C6	1.468 (8)	Mn1—O1	2.191 (4)
C6—N2	1.339 (7)	Mn1—O3ⁱ	2.208 (3)
C6—C7	1.392 (8)	O3—Mn1ⁱⁱ	2.208 (3)
C7—C8	1.357 (10)	O4—Mn1ⁱⁱ	2.150 (3)
C7—H7	0.9300	O1W—H1W	0.83 (5)
C8—N3	1.329 (8)	O1W—H2W	0.82 (4)
C8—H8	0.9300	O2W—H3W	0.82 (5)
C9—O1	1.250 (6)

N1—C1—C2	122.7 (6)	C1—N1—C5	117.8 (5)
N1—C1—H1	118.7	C1—N1—Mn1	125.8 (4)
C2—C1—H1	118.7	C5—N1—Mn1	116.2 (3)
C3—C2—C1	119.2 (6)	C6—N2—N3	105.2 (4)
C3—C2—H2	120.4	C6—N2—Mn1	117.0 (3)
C1—C2—H2	120.4	N3—N2—Mn1	137.6 (4)
C2—C3—C4	119.0 (6)	C8—N3—N2	111.5 (5)
C2—C3—H3	120.5	C8—N3—H3A	124.2
C4—C3—H3	120.5	N2—N3—H3A	124.2
C3—C4—C5	119.5 (6)	O4ⁱ—Mn1—O2	92.44 (13)
C3—C4—H4	120.3	O4ⁱ—Mn1—O1	159.58 (14)
C5—C4—H4	120.3	O2—Mn1—O1	75.93 (13)
N1—C5—C4	121.7 (5)	O4ⁱ—Mn1—O3ⁱ	76.27 (12)
N1—C5—C6	115.5 (4)	O2—Mn1—O3ⁱ	102.10 (16)
C4—C5—C6	122.8 (5)	O1—Mn1—O3ⁱ	89.63 (13)
N2—C6—C7	110.1 (5)	O4ⁱ—Mn1—N2	99.67 (15)
N2—C6—C5	118.1 (4)	O2—Mn1—N2	161.17 (16)
C7—C6—C5	131.8 (5)	O1—Mn1—N2	96.12 (15)
C8—C7—C6	105.4 (6)	O3ⁱ—Mn1—N2	94.79 (14)
C8—C7—H7	127.3	O4ⁱ—Mn1—N1	100.36 (14)
C6—C7—H7	127.3	O2—Mn1—N1	90.74 (16)
N3—C8—C7	107.8 (6)	O1—Mn1—N1	96.58 (15)
N3—C8—H8	126.1	O3ⁱ—Mn1—N1	166.79 (15)
C7—C8—H8	126.1	N2—Mn1—N1	73.01 (16)
O1—C9—O3	126.2 (4)	C9—O1—Mn1	114.4 (3)
O1—C9—C10	117.0 (4)	C10—O2—Mn1	115.4 (3)
O3—C9—C10	116.8 (4)	C9—O3—Mn1ⁱⁱ	114.0 (3)
O2—C10—O4	126.4 (4)	C10—O4—Mn1ⁱⁱ	115.7 (3)
O2—C10—C9	116.5 (4)	H1W—O1W—H2W	114 (4)
O4—C10—C9	117.1 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1W	0.86	1.89	2.748 (7)	175
O1W—H1W···O1ⁱⁱⁱ	0.83 (5)	2.08 (4)	2.851 (6)	155 (6)
O1W—H2W···O2W^iv	0.82 (4)	2.10 (5)	2.819 (6)	148 (6)
O2W—H3W···O3^v	0.82 (5)	2.06 (4)	2.823 (4)	156 (6)

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

Experimental details

Crystal data
Chemical formula	[Mn(C₂O₄)(C₈H₇N₃)]·1.5H₂O
M_r	315.15
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	29.460 (8), 9.236 (3), 9.875 (3)
β (°)	102.706 (5)
V (Å³)	2621.0 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.43 × 0.28 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.665, 0.805
No. of measured, independent and observed [I > 2σ(I)] reflections	6809, 2438, 2004
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.078, 1.00
No. of reflections	2438
No. of parameters	186
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.17

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL97 (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Mn1—N1	2.280 (4)	Mn1—O2	2.168 (3)
Mn1—N2	2.223 (4)	Mn1—O1	2.191 (4)
Mn1—O4ⁱ	2.150 (3)	Mn1—O3ⁱ	2.208 (3)

N2—Mn1—N1	73.01 (16)

Symmetry code: (i) x, −y, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1W	0.86	1.89	2.748 (7)	175
O1W—H1W···O1ⁱⁱ	0.83 (5)	2.08 (4)	2.851 (6)	155 (6)
O1W—H2W···O2Wⁱⁱⁱ	0.82 (4)	2.10 (5)	2.819 (6)	148 (6)
O2W—H3W···O3^iv	0.82 (5)	2.06 (4)	2.823 (4)	156 (6)

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

Acknowledgements

The authors acknowledge financial support from the program for talent introduction in Guangdong Higher Education Institutions and the scientific research start-up funds of talent introduction in Maoming University.

References

Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ward, M. D., Fleming, J. S., Psillakis, E., Jeffery, J. C. & McCleverty, J. A. (1998). Acta Cryst. C54, 609–612. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ward, M. D., McCleverty, J. A. & Jeffery, J. C. (2001). Coord. Chem. Rev. 222, 251–272. Web of Science CrossRef CAS Google Scholar

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

catena-Poly[[[[3-(2-pyrid­yl)-1H-pyrazole]manganese(II)]-μ-oxalato] sesquihydrate]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

catena-Poly[[[[3-(2-pyridyl)-1H-pyrazole]manganese(II)]-μ-oxalato] sesquihydrate]