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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): m801.
Published online 2008 May 10. doi:  10.1107/S160053680801369X
PMCID: PMC2961442

Diaqua­bis[3-(2-hydroxy­ethyl)-2-methyl-4-oxopyrido[1,2-a]pyrimidin-9-olato-κ2 N 1,O 9]manganese(II)

Abstract

The title compound, [Mn(C11H11N2O3)2(H2O)2], consists of discrete mononuclear complex mol­ecules. The MnII atom is located on an inversion center and coordinated by two N atoms and two O atoms, each pair in a trans mode, from two 3-(2-hydroxy­ethyl)-2-methyl-4-oxopyrido[1,2-a]pyrimidin-9-olate ligands and by two water mol­ecules. The coordination geometry around the MnII atom is slightly distorted octa­hedral. Mol­ecules are linked by O—H(...)O hydrogen bonds into a three-dimensional network.

Related literature

For related literature, see: Bayot et al. (2006 [triangle]); Chen et al. (2007 [triangle]); Wu et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m801-scheme1.jpg

Experimental

Crystal data

  • [Mn(C11H11N2O3)2(H2O)2]
  • M r = 529.41
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m801-efi1.jpg
  • a = 5.2656 (11) Å
  • b = 14.620 (3) Å
  • c = 14.715 (3) Å
  • β = 97.35 (3)°
  • V = 1123.5 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.65 mm−1
  • T = 293 (2) K
  • 0.15 × 0.12 × 0.06 mm

Data collection

  • Rigaku Scxmini 1K CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.904, T max = 0.965
  • 9361 measured reflections
  • 1971 independent reflections
  • 1553 reflections with I > 2σ(I)
  • R int = 0.063

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.108
  • S = 1.04
  • 1971 reflections
  • 172 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801369X/hy2131sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801369X/hy2131Isup2.hkl

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

supplementary crystallographic information

Comment

In the past decade, much attention has been paid to the design and synthesis of self-assembling systems with organic ligands containing N and O donors (Bayot et al., 2006; Chen et al., 2007). Quinolin-8-ol is such a ligand and the crystal structure of a complex containing it has been reported (Wu et al., 2006). We report here the synthesis and crystal structure of the title compound.

In the title compound (Fig. 1), the MnII atom is located on a crystallographic inversion center and adopts a distorted octahedral coordination geometry. The coordination environment is defined by two N atoms and two O atoms from two ligands in the equatorial plane and by two water molecules in the axial positions (Table 1). Intermolecular O—H···O hydrogen bonds involving the hydroxyl groups and water molecules as donors connect the molecules into a three-dimensional network (Table 2; Fig. 2).

Experimental

Manganese carbonate (0.028 g, 0.1 mmol) was added with constant stirring to a ethanol solution (10 ml) containing 3-(2-hydroxyethyl)-2-methyl-9-hydroxylpyrido[1,2-a]pyrimidin-4-one (0.022 g, 0.1 mmol). The mixture was then filtered off. After a few days, brown single crystals in the form of rectangular blocks deposited. They were separated off, washed with cold ethanol and dried in air at room temperature.

Refinement

H atoms bound to C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic), 0.97 (CH2) and 0.96 Å (CH3) and Uiso(H) = 1.2(or 1.5 for methyl)Ueq(C). H atoms of hydroxyl group and water molecule were located in a difference Fourier map and refined isotropically, with a restraint of O—H = 0.82 (1) Å for the hydroxyl group.

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) -x, -y + 2, -z + 1.]
Fig. 2.
Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines. H atoms have been omitted for clarity.

Crystal data

[Mn(C11H11N2O3)2(H2O)2]F000 = 550
Mr = 529.41Dx = 1.565 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4792 reflections
a = 5.2656 (11) Åθ = 3.1–25.0º
b = 14.620 (3) ŵ = 0.65 mm1
c = 14.715 (3) ÅT = 293 (2) K
β = 97.35 (3)ºBlock, brown
V = 1123.5 (4) Å30.15 × 0.12 × 0.06 mm
Z = 2

Data collection

Rigaku Scxmini 1K CCD area-detector diffractometer1971 independent reflections
Radiation source: fine-focus sealed tube1553 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.063
Detector resolution: 8.192 pixels mm-1θmax = 25.0º
T = 293(2) Kθmin = 3.1º
thin–slice ω scansh = −6→6
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)k = −17→17
Tmin = 0.904, Tmax = 0.965l = −17→17
9361 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108  w = 1/[σ2(Fo2) + (0.0407P)2 + 1.0124P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1971 reflectionsΔρmax = 0.27 e Å3
172 parametersΔρmin = −0.25 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
Mn10.00001.00000.50000.0287 (2)
N2−0.0870 (5)0.71347 (17)0.40610 (17)0.0305 (6)
C80.2483 (6)0.7863 (2)0.5424 (2)0.0299 (7)
C70.2868 (6)0.6962 (2)0.5179 (2)0.0331 (7)
C1−0.1042 (6)0.8032 (2)0.4332 (2)0.0276 (7)
C60.1200 (6)0.6554 (2)0.4466 (2)0.0349 (8)
C2−0.3130 (6)0.8590 (2)0.3894 (2)0.0304 (7)
C3−0.4831 (6)0.8190 (2)0.3220 (2)0.0358 (8)
H3A−0.61640.85340.29180.043*
C100.4954 (6)0.6367 (2)0.5655 (2)0.0374 (8)
H10A0.63670.67480.59200.045*
H10B0.55830.59620.52120.045*
C4−0.4570 (7)0.7271 (2)0.2988 (2)0.0415 (8)
H4A−0.57630.70110.25410.050*
C90.4222 (6)0.8307 (2)0.6180 (2)0.0391 (8)
H9A0.36790.89260.62570.059*
H9B0.59420.83060.60290.059*
H9C0.41620.79750.67390.059*
C110.3977 (7)0.5808 (2)0.6400 (2)0.0424 (9)
H11A0.32160.62160.68100.051*
H11B0.26450.53990.61240.051*
N10.0601 (4)0.83949 (17)0.49945 (17)0.0287 (6)
C5−0.2638 (6)0.6753 (2)0.3393 (2)0.0385 (8)
H5A−0.24930.61430.32260.046*
O1W0.1917 (5)1.00410 (18)0.37828 (18)0.0403 (6)
O20.1298 (5)0.57713 (15)0.41699 (17)0.0468 (6)
O1−0.3258 (4)0.94368 (14)0.41643 (15)0.0343 (5)
O30.5924 (5)0.52796 (17)0.69223 (16)0.0471 (6)
H1WB0.144 (7)0.995 (3)0.323 (3)0.048 (11)*
H1WA0.339 (9)0.986 (3)0.388 (3)0.077 (16)*
H3B0.653 (8)0.495 (2)0.657 (2)0.070 (15)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn10.0246 (3)0.0276 (4)0.0328 (4)0.0007 (3)−0.0004 (3)−0.0054 (3)
N20.0335 (14)0.0257 (14)0.0325 (15)0.0011 (11)0.0045 (12)−0.0006 (11)
C80.0295 (16)0.0291 (17)0.0313 (17)−0.0005 (14)0.0046 (13)0.0042 (13)
C70.0350 (18)0.0299 (18)0.0349 (18)0.0028 (14)0.0063 (14)0.0035 (14)
C10.0286 (16)0.0254 (16)0.0301 (16)−0.0011 (13)0.0085 (13)0.0006 (13)
C60.0389 (18)0.0293 (18)0.0374 (18)0.0045 (14)0.0083 (15)0.0032 (14)
C20.0264 (16)0.0314 (17)0.0340 (18)−0.0011 (13)0.0059 (13)−0.0006 (14)
C30.0325 (17)0.0357 (18)0.0368 (19)−0.0002 (14)−0.0045 (14)−0.0035 (14)
C100.0375 (18)0.0300 (18)0.044 (2)0.0045 (15)0.0041 (15)0.0037 (15)
C40.041 (2)0.042 (2)0.039 (2)−0.0059 (16)−0.0030 (16)−0.0081 (16)
C90.0379 (19)0.0322 (18)0.044 (2)0.0029 (15)−0.0067 (15)−0.0009 (15)
C110.043 (2)0.040 (2)0.043 (2)0.0061 (16)0.0035 (16)0.0033 (16)
N10.0252 (14)0.0262 (14)0.0332 (14)−0.0008 (10)−0.0016 (12)0.0000 (11)
C50.045 (2)0.0322 (18)0.0376 (19)−0.0078 (16)0.0025 (16)−0.0091 (15)
O1W0.0290 (13)0.0563 (16)0.0350 (14)0.0032 (13)0.0015 (10)−0.0080 (13)
O20.0568 (16)0.0277 (13)0.0552 (16)0.0052 (11)0.0045 (12)−0.0095 (11)
O10.0263 (11)0.0286 (12)0.0456 (13)0.0031 (9)−0.0047 (10)−0.0063 (10)
O30.0625 (17)0.0437 (15)0.0330 (14)0.0158 (13)−0.0024 (12)0.0027 (11)

Geometric parameters (Å, °)

Mn1—O1i2.143 (2)C2—C31.378 (4)
Mn1—O12.143 (2)C3—C41.398 (5)
Mn1—O1Wi2.166 (2)C3—H3A0.9300
Mn1—O1W2.166 (2)C10—C111.510 (5)
Mn1—N1i2.368 (2)C10—H10A0.9700
Mn1—N12.368 (2)C10—H10B0.9700
N2—C11.378 (4)C4—C51.346 (5)
N2—C51.382 (4)C4—H4A0.9300
N2—C61.448 (4)C9—H9A0.9600
C8—N11.351 (4)C9—H9B0.9600
C8—C71.387 (4)C9—H9C0.9600
C8—C91.495 (4)C11—O31.425 (4)
C7—C61.411 (5)C11—H11A0.9700
C7—C101.502 (4)C11—H11B0.9700
C1—N11.328 (4)C5—H5A0.9300
C1—C21.453 (4)O1W—H1WB0.81 (4)
C6—O21.228 (4)O1W—H1WA0.82 (5)
C2—O11.304 (4)O3—H3B0.80 (3)
O1i—Mn1—O1180.0C2—C3—H3A119.7
O1i—Mn1—O1Wi87.69 (9)C4—C3—H3A119.7
O1—Mn1—O1Wi92.31 (9)C7—C10—C11110.8 (3)
O1i—Mn1—O1W92.31 (9)C7—C10—H10A109.5
O1—Mn1—O1W87.69 (9)C11—C10—H10A109.5
O1Wi—Mn1—O1W180.000 (1)C7—C10—H10B109.5
O1i—Mn1—N1106.56 (8)C11—C10—H10B109.5
O1—Mn1—N173.44 (8)H10A—C10—H10B108.1
O1Wi—Mn1—N192.98 (9)C5—C4—C3121.7 (3)
O1W—Mn1—N187.02 (9)C5—C4—H4A119.2
O1i—Mn1—N1i73.44 (8)C3—C4—H4A119.2
O1—Mn1—N1i106.56 (8)C8—C9—H9A109.5
O1Wi—Mn1—N1i87.02 (9)C8—C9—H9B109.5
O1W—Mn1—N1i92.98 (9)H9A—C9—H9B109.5
N1—Mn1—N1i180.000 (1)C8—C9—H9C109.5
C1—N2—C5121.9 (3)H9A—C9—H9C109.5
C1—N2—C6120.8 (3)H9B—C9—H9C109.5
C5—N2—C6117.3 (3)O3—C11—C10113.4 (3)
N1—C8—C7123.1 (3)O3—C11—H11A108.9
N1—C8—C9116.2 (3)C10—C11—H11A108.9
C7—C8—C9120.7 (3)O3—C11—H11B108.9
C8—C7—C6119.8 (3)C10—C11—H11B108.9
C8—C7—C10123.4 (3)H11A—C11—H11B107.7
C6—C7—C10116.8 (3)C1—N1—C8118.9 (3)
N1—C1—N2122.2 (3)C1—N1—Mn1108.89 (18)
N1—C1—C2119.1 (3)C8—N1—Mn1131.21 (19)
N2—C1—C2118.7 (3)C4—C5—N2119.3 (3)
O2—C6—C7127.4 (3)C4—C5—H5A120.3
O2—C6—N2117.6 (3)N2—C5—H5A120.3
C7—C6—N2115.0 (3)Mn1—O1W—H1WB134 (3)
O1—C2—C3124.6 (3)Mn1—O1W—H1WA113 (3)
O1—C2—C1117.6 (3)H1WB—O1W—H1WA106 (4)
C3—C2—C1117.8 (3)C2—O1—Mn1118.08 (18)
C2—C3—C4120.6 (3)C11—O3—H3B107 (3)
N1—C8—C7—C6−2.0 (5)C7—C10—C11—O3−175.6 (3)
C9—C8—C7—C6179.8 (3)N2—C1—N1—C8−0.9 (4)
N1—C8—C7—C10−179.9 (3)C2—C1—N1—C8177.5 (3)
C9—C8—C7—C101.8 (5)N2—C1—N1—Mn1168.9 (2)
C5—N2—C1—N1177.7 (3)C2—C1—N1—Mn1−12.6 (3)
C6—N2—C1—N1−2.6 (4)C7—C8—N1—C13.3 (4)
C5—N2—C1—C2−0.7 (4)C9—C8—N1—C1−178.4 (3)
C6—N2—C1—C2179.0 (3)C7—C8—N1—Mn1−163.9 (2)
C8—C7—C6—O2179.6 (3)C9—C8—N1—Mn114.4 (4)
C10—C7—C6—O2−2.3 (5)O1i—Mn1—N1—C1−166.19 (19)
C8—C7—C6—N2−1.4 (4)O1—Mn1—N1—C113.81 (19)
C10—C7—C6—N2176.6 (3)O1Wi—Mn1—N1—C1105.3 (2)
C1—N2—C6—O2−177.3 (3)O1i—Mn1—N1—C82.0 (3)
C5—N2—C6—O22.4 (4)O1—Mn1—N1—C8−178.0 (3)
C1—N2—C6—C73.6 (4)O1Wi—Mn1—N1—C8−86.5 (3)
C5—N2—C6—C7−176.7 (3)O1W—Mn1—N1—C893.5 (3)
N1—C1—C2—O11.3 (4)C3—C4—C5—N20.4 (5)
N2—C1—C2—O1179.8 (3)C1—N2—C5—C40.7 (5)
N1—C1—C2—C3−178.9 (3)C6—N2—C5—C4−179.0 (3)
N2—C1—C2—C3−0.4 (4)C3—C2—O1—Mn1−166.9 (2)
O1—C2—C3—C4−178.8 (3)C1—C2—O1—Mn112.9 (3)
C1—C2—C3—C41.4 (5)O1Wi—Mn1—O1—C2−106.8 (2)
C8—C7—C10—C1194.0 (4)O1W—Mn1—O1—C273.2 (2)
C6—C7—C10—C11−84.0 (4)N1—Mn1—O1—C2−14.4 (2)
C2—C3—C4—C5−1.5 (5)N1i—Mn1—O1—C2165.6 (2)

Symmetry codes: (i) −x, −y+2, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1WB···O3ii0.83 (4)1.94 (5)2.761 (4)171 (4)
O1W—H1WA···O1iii0.81 (5)1.87 (5)2.680 (3)177 (5)
O3—H3B···O2iv0.80 (3)1.98 (4)2.772 (4)168 (4)

Symmetry codes: (ii) x−1/2, −y+3/2, z−1/2; (iii) x+1, y, z; (iv) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2131).

References

  • Bayot, D., Degand, M., Tinant, B. & Devillers, M. (2006). Inorg. Chem. Commun.359, 1390–1394.
  • Chen, K., Zhang, Y.-L., Feng, M.-Q. & Liu, C.-H. (2007). Acta Cryst. E63, m2033.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wu, H., Dong, X.-W., Liu, H.-Y. & Ma, J.-F. (2006). Acta Cryst. E62, m281–m282.

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