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In the title one-dimensional coordination polymer, {[Mn(C5O5)(C10H8N2)(H2O)]·H2O}n, each MnII ion is seven-coordinated by four O atoms from two croconate ligands, two N atoms from a 2,2′-bipyridine (2,2′-bipy) ligand and one O atom from an aqua ligand. The croconate ligand bridges the MnII ions in a bis-bidentate chelation mode, forming an extended [Mn(C5O5)]n chain running parallel to the [001] direction, with the lipophilic 2,2′-bipy ligands lying along one side and the hydro­philic water mol­ecules along the opposite side. Coordinated water and solvent water mol­ecules are arranged in the hydro­philic layer, which is characterized by O—H...O hydrogen bonds between croconate ligands. Meanwhile, 2,2′-bipy ligands from adjacent chains partially overlap and exhibit π–π inter­actions to form a lipophilic layer. The hydro­philic and lipophilic layers are arranged alternately to build a layer structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110006979/ln3137sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110006979/ln3137Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110006979/ln3137IIsup3.hkl
Contains datablock II

CCDC references: 774878; 774879

Comment top

The chemistry of the croconate dianion (C5O52-) dates from 1825 (Gmelin, 1825). In recent years, the coordination chemistry of the croconate ligand has attracted much attention because of its capability of constructing various one- to three-dimensional frameworks. One or two croconate ligands can bidentately chelate a metal ion to form [M(C5O5)] (Brouca-Cabarrecq & Trombe, 1992a,b) or [M(C5O5)2] complexes (Chen et al., 2005). Various croconato–metal frameworks with three to five O atoms involved in coordination and bridging have also been formed (Glick & Dahl, 1966; Brouca-Cabarrecq & Trombe, 1992a,b; Cornia et al., 1993; Maji et al., 2003). We have previously reported several mixed-ligand complexes formulated as [M(C5O5)(phen)2] (phen = 1,10-phenanthroline; Chen et al., 2007; Chen, Chen et al., 2008). Within this series, [Mn(C5O5)(phen)2] (Reference?) and [Cu(C5O5)(phen)2] (Reference?) crystallize in space group C2/c, while [Co(C5O5)(phen)2] (Reference?) and [Ni(C5O5)(phen)2] (Reference?) crystallize in space group Pbcn. These complexes do not show polymeric network structures.

2,2'-Bipyridine (2,2'-bipy) also has excellent chelating and π-conjugation ability. However, in comparison with phen, it has greater structural flexibility and has accordingly been used to build supramolecular architectures (Sun et al., 2005). We therefore chose 2,2'-bipy in place of phen to develop new mixed-ligand complexes and [Ni(C5O5)(2,2'-bipy)2] was thus obtained (Chen, Fang & Yu, 2008). This complex is isostructural with [Ni(C5O5)(phen)2] and also shows an isolated structure. Recently, we synthesized the title mixed-ligand complex, {[Mn(C5O5)(2,2'-bipy)(H2O)].H2O}n, (I), which shows a bis-bidentate bridging mode and a one-dimensional polymeric structure. We report here its crystal structure at 135 K. The structure at 291 K has also been determined; it is essentially the same as that at 135 K, and the data have been deposited in the Supplementary Material. Note that in all of our previous or present mixed-ligand complexes, the neutral phen or 2,2'-bipy ligands are essentially lipophilic, while the croconate anion is prone to be hydrophilic, and its alkali metal salts can easily dissolve in water.

As shown in Fig. 1, the asymmetric unit of (I) comprises an MnII ion and three different ligands, with a solvent water molecule linking to the aqua ligand via a hydrogen bond. The seven coordinating atoms make up a severely distorted pentagonal bipyramid. Atoms O6 and N1 are in axial positions, with the O6—Mn1—N1 moiety being essentially collinear [170.14 (3)°] and with the Mn1—O6(aqua) bond length [2.1484 (8) Å] being the shortest in the MnO5N2 coordination polyhedron. Among the five equatorial atoms, O1 and N2 are displaced by -0.800 (1) and 1.582 (1) Å, respectively, on opposite sides of the plane defined by atoms O2, O3 and O4. The terminal C15—O5 bond shows the `ketonic' CO bond length [1.2360 (10) Å], while the other four C—O bonds involved in coordination show longer C—O distances.

The croconate ligand is bridging, and exhibits a bis-bidentate chelation mode through four O atoms to two MnII ions. In this way, an infinite one-dimensional coordination chain is formed along the [001] direction (Fig. 2), in which the zigzag-arranged MnII ions are the nodes connecting a series of planar croconate ligands. The planes of two neighbouring croconate ligands in the chain have a dihedral angle of 22.7 (1)° and the two carbonyl groups point to opposite sides of the chain. Along the [Mn(C5O5)]n chain, 2,2'-bipy ligands are attached to the same side, forming the lipophilic side of the chain. The least-squares plane of the 2,2'-bipy ligand is roughly perpendicular to those of the two croconate ligands coordinated to the same MnII ion, with dihedral angles of 89.3 (1) and 84.6 (1)°. The aqua ligands, which lie trans to the 2,2'-bipy ligands, form the hydrophilic side of the [Mn(C5O5)]n chain. The [Mn(C5O5)]n chains run parallel to c-glide planes, with the croconate ligands lying across these glide planes. The dihedral angle between the glide plane and the plane of the croconate ligand is 81.5 (1)°, and that between the glide plane and the plane of the 2,2'-bipy ligand is 77.9 (1)°.

To date, several polymeric mixed-ligand croconate complexes have been reported. In the one-dimensional coordination polymer {[Co2(C5O5)2(bpds)2(H2O)4].3H2O}n (bpds = 4,4'-bipyridyl disulfide), the terminal-bidentate croconate ligand is at the side of the [Co(bpds)]n main chain (Manna et al., 2007). In comparison with 2,2'-bipy, 4,4'-bipyridine (4,4'-bipy) is a bridging ligand that is useful for the construction of two-dimensional frameworks. The [Cd2(C5O5)2(4,4'-bipy)(H2O)]n complex (Wang et al., 2003) and the isostructural {[Cd2(C5O5)2(bipye)(H2O)].2H2O}n [bipye = 1,2-bis(4-pyridyl)ethylene; Wang, Tseng et al., 2007] complexes exhibit a tightly-bonded bilayer two-dimensional framework, which is characterized by a tris-bidentate bridging mode in the [Cd(C5O5)]n chain. The {[Cu2(C5O5)2(bipye)2].H2O}n complex shows an undulating monolayer two-dimensional framework (Ghoshal et al., 2005), while {[Zn2(C5O5)2(bipye)2].H2O}n (Wang, Tseng et al., 2007) exhibits a brick-wall-like two-dimensional structure. Similar bilayer two-dimensional frameworks can be found in the group of isostructural complexes [M(C5O5)(bipya)]n [M = Mn, Fe, Co, Cd; bipya = 1,2-bis(4-pyridyl)ethane; Wang, Dai et al., 2007]. Small ligands such as pyrazine (Maji et al., 2004) or polydentate N,N'-bis(3-aminopropyl)oxamide (Castro et al., 2001) are also involved in two-dimensional mixed-ligand frameworks. One could consider that the 2,2'-bipyrimidine (bipym) ligand combines the properties of bidentate 2,2'-bipy and bridgeable 4,4'-bipy, and it has thus been employed to enhance dimensionality. However, the [Cd2(C5O5)2(bipym)(H2O)2]n structure also shows a two-dimensional framework (Wang, Kuo et al., 2007), in which the [Cd(C5O5)]n chain is similar to the [Mn(C5O5)]n chain of (I).

Fig. 3 shows a projection looking along a bundle of polymeric coordination chains of (I) (along the c direction), which are cross-linked by hydrogen bonding and ππ interactions. Coordinated water and solvent water molecules from neighbouring chains come together to form a hydrophilic layer, and 2,2'-bipy ligands from adjacent chains form a lipophilic layer. The hydrophilic and lipophilic layers are stacked alternately to build a layer structure.

The detailed hydrophilic–hydrophilic interactions are exhibited in Fig. 2 and Table 2, and involve four unique O—H···O hydrogen bonds. Both the coordinated water and the solvent water molecules act as double hydrogen-bond donors in these hydrogen bonds, and the latter also acts as a single hydrogen-bond acceptor. Besides hydrogen bonding, there are several short intermolecular C···O and C···C contacts involving the CO group in the hydrophilic layer: the C14···O5iv, C14···C15iv and C15···C15iv distances are 2.9002 (11), 3.1888 (12) and 3.1170 (12) Å, respectively [symmetry code: (iv) -x + 1, -y + 1, -z + 2]. These interactions may also considered to be ππ interactions between the CO group and an adjacent croconate C5 ring, as these two entities are parallel.

As shown in Fig. 2, the lipophilic layer is characterized by ππ interactions in 2,2'-bipy pairs between neighbouring [Mn(C5O5)]n chains. The cross-linking of the chains through these ππ interactions is further assisted by the C7—H7···O2(-x + 2, -y, -z + 2) interaction. The 2,2'-bipy ligand is basically planar, with a small dihedral angle of 9.4 (1)° between its two pyridine rings as a result of the bidentate chelation balance and intra-ligand H···H repulsion. The two 2,2'-bipy ligands in the ππ interaction are approximately half-overlapped, with the interplanar spacing being 3.429 (5) Å (the spacing is based on the least-squares plane of the 2,2'-bipy ligand). The C5···C7(-x + 2, -y, -z + 2) distance of 3.2664 (13) Å in the 2,2'-bipy pair is slightly shorter than the interplanar spacing and is nearly perpendicular [85.1 (1)°] to these planes. Thus, the structural flexibility of the 2,2'-bipy ligand is manifested in (I). Using the rigid phen ligand and similar synthetic methods, the resultant [Mn(C5O5)(phen)2] complex does not show a network structure (Reference?). Note that [Ni(C5O5)(2,2'-bipy)2] also fails to form a network structure (Reference?). The half-empty d shell and the relatively large size of the Mn atom, which accommodates higher coordination numbers and has longer Mn—X bond lengths, may account for this difference. For example, the average Mn—N bond length in (I) [2.300 (2) Å] is much longer than the average Ni—N length [2.063 (3) Å] in [Ni(C5O5)(2,2'-bipy)2] at the same temperature (i.e. room temperature).

The unit-cell dimensions at 291 K are a = 11.3911 (2), b = 9.4023 (1) and c = 14.4361 (2) Å, β = 104.740 (1)° and V = 1495.26 (3) Å3 (see Supplementary Material). The cell dimensions contract anisotropically with decreasing temperature, with the largest contractions being perpendicular to the direction of the rigid chain, i.e. adjacent chains may be able to nestle closer to one another at lower temperature, thus increasing the strength of the intermolecular interactions.

The thermogravimetry (TG) curve (Fig. 4) of the title crystal exhibits three weight-loss steps. The first weight loss begins at 366 K and the weight approaches 95.4% of the original weight at 393 K, corresponding to the loss of a solvent water molecule. The differential thermal analysis (DTA) curve gives an enthalpy change of 46.8 kJ mol-1 for this dehydration process, indicating the very strong hydrogen bonding. The second weight loss begins at 422 K and the weight approaches 90.7% of the original weight at 503 K, which can be assigned to the release of the coordinated water molecule. In the DTA curve, the corresponding second valley suggests an enthalpy change of 43.1 kJ mol-1. The strength of hydrogen bonding here is comparable with the aqua coordination of the water molecule.

In conclusion, the one-dimensional molecular fibres of (I) have been woven into a three-dimensional structure by alternating layers of strong hydrophilic–hydrophilic interactions and lipophilic–lipophilic interactions.

Experimental top

[K2(C5O5)] (0.032 g, 0.15 mmol) and MnCl2.4H2O (0.044 g, 0.22 mmol) were separately dissolved in water (10 ml), and 2,2'-bipy (0.036 g, 0.23 mmol) was dissolved in ethanol (10 ml). These three solutions were then mixed. The mixture was filtered, giving a greenish-yellow solution. Pale-green prismatic crystals of (I) were obtained by slow evaporation of this solution at room temperature over several weeks. Analysis, found: C 45.97, N 7.45, H 3.05%; calculated for [Mn(C5O5)(C10H8N2)(H2O)].H2O: C 46.53, N 7.23, H 3.12%.

Refinement top

All H atoms were located in difference Fourier maps, and their positions and isotropic displacement parameters were refined freely. The C—H distances are in the range 0.941 (16)–0.984 (15) Å. There are relatively large differences between the anisotropic displacements along the Mn—O bonds [diff(Mn—O)] involving the two chelating rings. These may be due to the nature of the structure itself. The dominant ionic Mn—O coordination bonds are not as strong as a typical covalent bond. The MnII ion has seven Mn—X bonds and the MnO5N2 coordination polyhedron is totally asymmetric. The weak and multiple bonding in the coordination polyhedron may bring about some deviations from the Hirshfeld rigid-bond postulate (Hirshfeld, 1976). Lutz & Spek (2009) reported that certain Zn—O(carboxylate) coordination bonds fail the Hirshfeld rigid-bond postulate, which was attributed to steric strain in the chelate ring. Similar steric strain may also be present in (I). The five atoms in the equatorial position of the distorted MnO5N2 pentagonal bipyramid may be a little crowded. We note that diff(Mn1—N2) (8.7 s.u.) involving the equatorial atom N2 is larger than diff(Mn1—N1) (5.7 s.u.) involving the axial atom N1.

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The unique [Mn(C5O5)(2,2'-dipy)(H2O)].H2O moiety of (I) at 135 K, together with another `molecule' to show the ππ interactions and hydrogen bonds (dashed lines). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry codes: (i) x, -y + 1/2, z + 1/2; (v) -x + 2, -y, -z + 2.]
[Figure 2] Fig. 2. A side view of several [Mn(C5O5)]n chains in (I), showing the chain structure and the hydrophilic–hydrophilic and lipophilic–lipophilic interactions at 135 K. Dashed lines denote unique O—H···O and C—H···O hydrogen bonds and intermolecular C···C and C···O short contacts. [Symmetry codes: (ii) -x + 1, y - 1/2, -z + 3/2; (iii) -x + 1, -y, -z + 2; (iv) -x + 1, 1 - y, -z + 2; (v) -x + 2, -y, -z + 2.]
[Figure 3] Fig. 3. A projection of the bundle of [Mn(C5O5)]n chains along the chain direction (c direction) at 135 K, showing the alternate hydrophilic and lipophilic layers. Dashed lines denote O—H···O hydrogen bonds and intermolecular C···C and C···O short contacts.
[Figure 4] Fig. 4. The thermogravimetry (TG) curve of (I), together with the differential thermal (DTA) curve, with a heating rate of 10 K min-1 under a nitrogen atmosphere.
(I) Poly[[[aqua(2,2'-bipyridine-κ2N,N')manganese(II)]-µ- croconato-κ4O,O':O'',O'''] monohydrate] top
Crystal data top
[Mn(C5O5)(C10H8N2)(H2O)]·H2OF(000) = 788
Mr = 387.21Dx = 1.740 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9577 reflections
a = 11.3363 (2) Åθ = 2.6–33.1°
b = 9.3622 (1) ŵ = 0.94 mm1
c = 14.4053 (2) ÅT = 135 K
β = 104.8460 (6)°Prism, pale-green
V = 1477.84 (4) Å30.26 × 0.20 × 0.11 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5570 independent reflections
Radiation source: fine-focus sealed tube5142 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
Detector resolution: 10 pixels mm-1θmax = 33.0°, θmin = 1.9°
ϕ and ω scansh = 1717
Absorption correction: multi-scan
(APEX2; Bruker, 2005)
k = 1414
Tmin = 0.790, Tmax = 0.904l = 2022
33771 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024All H-atom parameters refined
wR(F2) = 0.064 w = 1/[σ2(Fo2) + (0.0316P)2 + 0.6657P]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.002
5570 reflectionsΔρmax = 0.50 e Å3
275 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0020 (4)
Crystal data top
[Mn(C5O5)(C10H8N2)(H2O)]·H2OV = 1477.84 (4) Å3
Mr = 387.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.3363 (2) ŵ = 0.94 mm1
b = 9.3622 (1) ÅT = 135 K
c = 14.4053 (2) Å0.26 × 0.20 × 0.11 mm
β = 104.8460 (6)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5570 independent reflections
Absorption correction: multi-scan
(APEX2; Bruker, 2005)
5142 reflections with I > 2σ(I)
Tmin = 0.790, Tmax = 0.904Rint = 0.018
33771 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0240 restraints
wR(F2) = 0.064All H-atom parameters refined
S = 0.99Δρmax = 0.50 e Å3
5570 reflectionsΔρmin = 0.31 e Å3
275 parameters
Special details top

Experimental. Scan width 0.3° ω, Crystal to detector distance 5.96 cm

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
xyzUiso*/Ueq
Mn10.684601 (11)0.136951 (13)0.798151 (9)0.01353 (4)
O10.64305 (6)0.36233 (7)0.84470 (5)0.01713 (12)
O20.69659 (6)0.12198 (7)0.96469 (5)0.01690 (12)
O30.68641 (7)0.28465 (8)0.66655 (5)0.02153 (13)
O40.64686 (6)0.01037 (7)0.66163 (5)0.01967 (12)
O50.60917 (6)0.61730 (7)0.96076 (5)0.01930 (12)
O60.50163 (7)0.06724 (10)0.78987 (6)0.02909 (17)
H6A0.4708 (15)0.0771 (18)0.8352 (12)0.035 (4)*
H6B0.4651 (16)0.012 (2)0.7534 (14)0.043 (5)*
O70.40443 (8)0.11709 (9)0.94229 (7)0.02875 (17)
H7A0.3853 (17)0.055 (2)0.9735 (14)0.053 (5)*
H7B0.4032 (17)0.191 (2)0.9712 (14)0.048 (5)*
N10.88715 (7)0.20062 (8)0.83436 (6)0.01642 (13)
N20.80304 (7)0.06249 (8)0.84553 (5)0.01566 (13)
C10.92428 (9)0.33343 (10)0.82123 (7)0.01973 (16)
H10.8590 (13)0.4009 (15)0.7978 (10)0.024 (3)*
C21.04630 (9)0.36918 (10)0.83453 (7)0.02126 (17)
H21.0695 (13)0.4666 (16)0.8253 (10)0.024 (3)*
C31.13363 (9)0.26271 (11)0.86028 (7)0.02256 (17)
H31.2189 (14)0.2795 (17)0.8680 (11)0.033 (4)*
C41.09650 (8)0.12501 (10)0.87448 (7)0.02093 (17)
H41.1554 (14)0.0518 (17)0.8943 (11)0.032 (4)*
C50.97229 (8)0.09781 (9)0.86212 (6)0.01548 (14)
C60.92508 (8)0.04680 (9)0.87424 (6)0.01500 (14)
C71.00256 (9)0.16065 (10)0.91059 (7)0.02089 (16)
H71.0909 (13)0.1435 (14)0.9336 (11)0.023 (3)*
C80.95203 (10)0.29509 (10)0.91378 (8)0.02414 (18)
H81.0020 (15)0.3742 (16)0.9369 (12)0.032 (4)*
C90.82694 (10)0.31224 (10)0.88098 (8)0.02464 (19)
H90.7906 (14)0.4040 (17)0.8810 (11)0.030 (4)*
C100.75550 (9)0.19272 (10)0.84857 (7)0.02112 (17)
H100.6684 (14)0.2011 (17)0.8260 (11)0.030 (4)*
C110.64960 (7)0.36809 (9)0.93330 (6)0.01355 (13)
C120.67600 (7)0.24299 (9)0.99502 (6)0.01342 (13)
C130.67313 (7)0.28685 (9)1.09142 (6)0.01509 (14)
C140.65074 (7)0.44100 (9)1.08891 (6)0.01466 (14)
C150.63350 (7)0.49386 (9)0.98982 (6)0.01401 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.01516 (6)0.01414 (6)0.01166 (6)0.00095 (4)0.00411 (4)0.00048 (4)
O10.0235 (3)0.0180 (3)0.0108 (3)0.0034 (2)0.0059 (2)0.0003 (2)
O20.0205 (3)0.0154 (3)0.0152 (3)0.0020 (2)0.0054 (2)0.0009 (2)
O30.0306 (3)0.0219 (3)0.0121 (3)0.0001 (3)0.0055 (2)0.0023 (2)
O40.0257 (3)0.0211 (3)0.0136 (3)0.0037 (2)0.0077 (2)0.0049 (2)
O50.0238 (3)0.0151 (3)0.0200 (3)0.0014 (2)0.0075 (2)0.0006 (2)
O60.0223 (3)0.0439 (5)0.0237 (4)0.0131 (3)0.0109 (3)0.0170 (3)
O70.0358 (4)0.0219 (3)0.0351 (4)0.0014 (3)0.0210 (3)0.0039 (3)
N10.0173 (3)0.0149 (3)0.0172 (3)0.0003 (2)0.0047 (2)0.0007 (2)
N20.0167 (3)0.0151 (3)0.0161 (3)0.0004 (2)0.0059 (2)0.0005 (2)
C10.0231 (4)0.0157 (3)0.0211 (4)0.0008 (3)0.0068 (3)0.0013 (3)
C20.0256 (4)0.0196 (4)0.0193 (4)0.0059 (3)0.0070 (3)0.0005 (3)
C30.0192 (4)0.0254 (4)0.0230 (4)0.0058 (3)0.0053 (3)0.0015 (3)
C40.0160 (3)0.0219 (4)0.0241 (4)0.0008 (3)0.0037 (3)0.0005 (3)
C50.0158 (3)0.0162 (3)0.0143 (3)0.0002 (3)0.0036 (3)0.0005 (3)
C60.0169 (3)0.0149 (3)0.0134 (3)0.0012 (3)0.0042 (3)0.0002 (3)
C70.0214 (4)0.0193 (4)0.0214 (4)0.0047 (3)0.0044 (3)0.0024 (3)
C80.0312 (5)0.0174 (4)0.0260 (5)0.0064 (3)0.0115 (4)0.0047 (3)
C90.0319 (5)0.0152 (4)0.0318 (5)0.0001 (3)0.0172 (4)0.0020 (3)
C100.0221 (4)0.0172 (4)0.0266 (5)0.0025 (3)0.0108 (3)0.0008 (3)
C110.0142 (3)0.0153 (3)0.0116 (3)0.0003 (2)0.0042 (2)0.0005 (2)
C120.0135 (3)0.0156 (3)0.0113 (3)0.0000 (2)0.0033 (2)0.0001 (3)
C130.0160 (3)0.0179 (3)0.0114 (3)0.0011 (3)0.0034 (3)0.0006 (3)
C140.0149 (3)0.0176 (3)0.0121 (3)0.0024 (3)0.0046 (3)0.0018 (3)
C150.0142 (3)0.0156 (3)0.0131 (3)0.0007 (2)0.0050 (3)0.0013 (3)
Geometric parameters (Å, º) top
Mn1—N12.2991 (8)C1—C21.3880 (14)
Mn1—N22.2990 (7)C1—H10.966 (14)
Mn1—O12.2990 (6)C2—C31.3867 (14)
Mn1—O22.3719 (7)C2—H20.968 (15)
Mn1—O32.3508 (7)C3—C41.3875 (14)
Mn1—O42.3499 (7)C3—H30.957 (16)
Mn1—O62.1484 (8)C4—C51.3967 (12)
O1—C111.2605 (10)C4—H40.948 (16)
O2—C121.2574 (10)C5—C61.4824 (12)
C13—O3i1.2484 (11)C6—C71.3950 (12)
C14—O4i1.2428 (10)C7—C81.3885 (14)
O3—C13ii1.2484 (11)C7—H70.984 (15)
O4—C14ii1.2428 (10)C8—C91.3844 (15)
O5—C151.2360 (10)C8—H80.941 (16)
O6—H6A0.820 (17)C9—C101.3900 (14)
O6—H6B0.779 (19)C9—H90.953 (16)
O7—H7A0.80 (2)C10—H100.960 (15)
O7—H7B0.81 (2)C11—C121.4544 (11)
N1—C11.3416 (11)C12—C131.4566 (12)
N1—C51.3491 (11)C13—C141.4641 (12)
N2—C61.3467 (11)C14—C151.4757 (12)
N2—C101.3382 (11)C11—C151.4693 (11)
O6—Mn1—O191.60 (3)C1—C2—H2120.3 (8)
O6—Mn1—N2104.59 (3)C2—C3—C4118.98 (9)
O1—Mn1—N2143.76 (3)C2—C3—H3122.9 (10)
O6—Mn1—N1170.14 (3)C4—C3—H3118.1 (10)
O1—Mn1—N187.89 (3)C3—C4—C5118.99 (9)
N2—Mn1—N170.72 (3)C3—C4—H4119.9 (10)
O6—Mn1—O478.99 (3)C5—C4—H4121.1 (10)
O1—Mn1—O4140.88 (2)N1—C5—C4121.94 (8)
N2—Mn1—O474.87 (2)N1—C5—C6115.72 (7)
N1—Mn1—O4107.41 (3)C4—C5—C6122.28 (8)
O6—Mn1—O3109.98 (3)N2—C6—C7122.03 (8)
O1—Mn1—O374.94 (2)N2—C6—C5115.91 (7)
N2—Mn1—O3126.30 (3)C7—C6—C5122.03 (8)
N1—Mn1—O379.39 (3)C8—C7—C6118.66 (9)
O4—Mn1—O373.00 (2)C8—C7—H7122.0 (8)
O6—Mn1—O280.94 (3)C6—C7—H7119.4 (8)
O1—Mn1—O273.87 (2)C9—C8—C7119.28 (9)
N2—Mn1—O276.94 (2)C9—C8—H8120.1 (10)
N1—Mn1—O289.47 (3)C7—C8—H8120.6 (10)
O4—Mn1—O2139.71 (2)C8—C9—C10118.61 (9)
O3—Mn1—O2147.17 (2)C8—C9—H9120.6 (9)
C11—O1—Mn1111.79 (5)C10—C9—H9120.7 (9)
C12—O2—Mn1109.30 (5)N2—C10—C9122.66 (9)
C13ii—O3—Mn1111.08 (6)N2—C10—H10116.8 (10)
C14ii—O4—Mn1111.13 (6)C9—C10—H10120.5 (10)
Mn1—O6—H6A121.5 (11)O1—C11—C12122.28 (7)
Mn1—O6—H6B125.4 (13)O1—C11—C15127.73 (8)
H6A—O6—H6B110.5 (17)C12—C11—C15110.00 (7)
H7A—O7—H7B107.0 (19)O2—C12—C11122.72 (7)
C1—N1—C5118.46 (8)O2—C12—C13129.56 (8)
C1—N1—Mn1122.65 (6)C11—C12—C13107.72 (7)
C5—N1—Mn1118.64 (6)O3i—C13—C12130.40 (8)
C10—N2—C6118.68 (8)O3i—C13—C14122.12 (8)
C10—N2—Mn1122.70 (6)C12—C13—C14107.48 (7)
C6—N2—Mn1118.58 (6)O4i—C14—C13122.52 (8)
N1—C1—C2122.80 (9)O4i—C14—C15127.99 (8)
N1—C1—H1114.5 (9)C13—C14—C15109.49 (7)
C2—C1—H1122.6 (9)O5—C15—C11127.61 (8)
C3—C2—C1118.78 (9)O5—C15—C14127.15 (8)
C3—C2—H2120.9 (8)C11—C15—C14105.23 (7)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6A···O70.820 (17)1.919 (18)2.7373 (12)175.0 (17)
O6—H6B···O1iii0.779 (19)2.137 (19)2.9153 (10)177.2 (18)
O7—H7A···O2iv0.80 (2)2.20 (2)2.9838 (11)169.1 (19)
O7—H7B···O5v0.81 (2)2.06 (2)2.8755 (11)176.8 (19)
C7—H7···O2vi0.984 (15)2.487 (15)3.4425 (12)163.8 (12)
Symmetry codes: (iii) x+1, y1/2, z+3/2; (iv) x+1, y, z+2; (v) x+1, y+1, z+2; (vi) x+2, y, z+2.
(II) Poly[[[aqua(2,2'-bipyridine-κ2N,N')manganese(II)]-µ- croconato-κ4O,O':O'',O'''] monohydrate] top
Crystal data top
[Mn(C5O5)(C10H8N2)(H2O)]·H2OF(000) = 788
Mr = 387.21Dx = 1.720 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6113 reflections
a = 11.3911 (2) Åθ = 2.9–27.5°
b = 9.4023 (1) ŵ = 0.93 mm1
c = 14.4361 (2) ÅT = 291 K
β = 104.740 (1)°Prism, pale-green
V = 1495.26 (3) Å30.50 × 0.17 × 0.13 mm
Z = 4
Data collection top
Bruker APEX2 CCD area-detector
diffractometer
3251 independent reflections
Radiation source: fine-focus sealed tube2966 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 10 pixels mm-1θmax = 27.0°, θmin = 1.9°
ϕ and ω scansh = 1414
Absorption correction: multi-scan
(APEX2; Bruker, 2005)
k = 128
Tmin = 0.654, Tmax = 0.889l = 1718
10311 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024All H-atom parameters refined
wR(F2) = 0.062 w = 1/[σ2(Fo2) + (0.0324P)2 + 0.654P]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max = 0.001
3251 reflectionsΔρmax = 0.27 e Å3
275 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0062 (6)
Crystal data top
[Mn(C5O5)(C10H8N2)(H2O)]·H2OV = 1495.26 (3) Å3
Mr = 387.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.3911 (2) ŵ = 0.93 mm1
b = 9.4023 (1) ÅT = 291 K
c = 14.4361 (2) Å0.50 × 0.17 × 0.13 mm
β = 104.740 (1)°
Data collection top
Bruker APEX2 CCD area-detector
diffractometer
3251 independent reflections
Absorption correction: multi-scan
(APEX2; Bruker, 2005)
2966 reflections with I > 2σ(I)
Tmin = 0.654, Tmax = 0.889Rint = 0.016
10311 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0240 restraints
wR(F2) = 0.062All H-atom parameters refined
S = 0.96Δρmax = 0.27 e Å3
3251 reflectionsΔρmin = 0.26 e Å3
275 parameters
Special details top

Experimental. Scan width 0.5° ω, Crystal to detector distance 6.02 cm

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
xyzUiso*/Ueq
Mn10.685703 (18)0.13748 (2)0.798547 (13)0.02386 (8)
O10.64361 (9)0.36163 (10)0.84543 (7)0.0293 (2)
O20.69761 (9)0.12284 (10)0.96504 (7)0.0291 (2)
O30.68758 (10)0.28426 (12)0.66611 (7)0.0373 (2)
O40.64784 (9)0.00889 (11)0.66128 (7)0.0342 (2)
O50.60963 (10)0.61501 (10)0.96111 (7)0.0331 (2)
O60.50393 (11)0.06671 (16)0.79010 (10)0.0490 (3)
H6A0.4694 (18)0.079 (2)0.8351 (15)0.053 (6)*
H6B0.469 (2)0.015 (2)0.7544 (17)0.058 (7)*
O70.40479 (13)0.11779 (17)0.94164 (11)0.0502 (3)
H7A0.385 (2)0.057 (3)0.9714 (19)0.084 (9)*
H7B0.402 (2)0.191 (3)0.9678 (18)0.075 (8)*
N10.88745 (10)0.20027 (12)0.83449 (8)0.0279 (2)
N20.80325 (10)0.06149 (12)0.84535 (8)0.0269 (2)
C10.92501 (15)0.33227 (16)0.82211 (11)0.0336 (3)
H10.8623 (15)0.4000 (19)0.7992 (12)0.036 (4)*
C21.04557 (15)0.36752 (17)0.83568 (11)0.0362 (3)
H21.0690 (16)0.461 (2)0.8277 (12)0.041 (5)*
C31.13186 (14)0.26196 (18)0.86124 (11)0.0384 (3)
H31.2137 (18)0.279 (2)0.8684 (13)0.048 (5)*
C41.09496 (14)0.12544 (18)0.87456 (12)0.0360 (3)
H41.1522 (17)0.051 (2)0.8943 (13)0.043 (5)*
C50.97164 (12)0.09809 (15)0.86180 (9)0.0261 (3)
C60.92461 (12)0.04632 (15)0.87346 (9)0.0259 (3)
C71.00084 (15)0.15974 (17)0.90884 (11)0.0351 (3)
H71.0874 (18)0.1466 (19)0.9314 (13)0.042 (5)*
C80.95076 (17)0.29293 (17)0.91223 (12)0.0414 (4)
H81.0004 (17)0.372 (2)0.9341 (13)0.045 (5)*
C90.82694 (17)0.30929 (17)0.88033 (13)0.0413 (4)
H90.7890 (17)0.401 (2)0.8795 (13)0.046 (5)*
C100.75643 (15)0.19115 (16)0.84863 (11)0.0354 (3)
H100.6698 (17)0.198 (2)0.8269 (13)0.044 (5)*
C110.65021 (11)0.36720 (14)0.93363 (9)0.0231 (3)
C120.67681 (11)0.24317 (14)0.99503 (9)0.0231 (3)
C130.67400 (12)0.28695 (15)1.09142 (9)0.0261 (3)
C140.65142 (11)0.43985 (15)1.08892 (9)0.0253 (3)
C150.63387 (11)0.49253 (14)0.98997 (9)0.0243 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.02616 (12)0.02487 (12)0.02091 (11)0.00186 (8)0.00666 (8)0.00096 (7)
O10.0394 (5)0.0314 (5)0.0185 (4)0.0059 (4)0.0098 (4)0.0007 (4)
O20.0344 (5)0.0275 (5)0.0256 (5)0.0040 (4)0.0080 (4)0.0012 (4)
O30.0518 (6)0.0387 (6)0.0205 (5)0.0001 (5)0.0079 (4)0.0042 (4)
O40.0437 (6)0.0371 (6)0.0243 (5)0.0064 (5)0.0133 (4)0.0092 (4)
O50.0398 (6)0.0262 (5)0.0350 (5)0.0018 (4)0.0127 (4)0.0001 (4)
O60.0378 (6)0.0727 (9)0.0404 (7)0.0202 (6)0.0171 (5)0.0274 (6)
O70.0584 (8)0.0396 (7)0.0632 (9)0.0016 (6)0.0348 (7)0.0066 (7)
N10.0292 (6)0.0263 (6)0.0285 (6)0.0000 (5)0.0080 (5)0.0004 (4)
N20.0286 (6)0.0268 (6)0.0268 (5)0.0006 (5)0.0097 (4)0.0008 (4)
C10.0393 (8)0.0279 (7)0.0345 (7)0.0003 (6)0.0112 (6)0.0020 (6)
C20.0451 (9)0.0323 (8)0.0324 (8)0.0117 (7)0.0120 (6)0.0015 (6)
C30.0318 (8)0.0442 (9)0.0388 (8)0.0103 (7)0.0082 (6)0.0033 (7)
C40.0276 (7)0.0385 (8)0.0404 (8)0.0006 (6)0.0060 (6)0.0010 (6)
C50.0271 (6)0.0290 (7)0.0218 (6)0.0002 (5)0.0054 (5)0.0012 (5)
C60.0286 (6)0.0281 (7)0.0216 (6)0.0024 (5)0.0073 (5)0.0014 (5)
C70.0344 (8)0.0342 (8)0.0357 (8)0.0073 (6)0.0071 (6)0.0034 (6)
C80.0544 (10)0.0301 (8)0.0431 (9)0.0129 (7)0.0187 (7)0.0084 (7)
C90.0541 (10)0.0249 (8)0.0530 (10)0.0019 (7)0.0285 (8)0.0018 (7)
C100.0366 (8)0.0297 (8)0.0440 (8)0.0044 (6)0.0178 (7)0.0017 (6)
C110.0208 (6)0.0283 (7)0.0202 (6)0.0003 (5)0.0053 (5)0.0014 (5)
C120.0201 (6)0.0281 (7)0.0206 (6)0.0003 (5)0.0042 (5)0.0015 (5)
C130.0245 (6)0.0334 (7)0.0200 (6)0.0025 (5)0.0049 (5)0.0006 (5)
C140.0229 (6)0.0317 (7)0.0222 (6)0.0053 (5)0.0070 (5)0.0049 (5)
C150.0219 (6)0.0276 (7)0.0241 (6)0.0018 (5)0.0074 (5)0.0029 (5)
Geometric parameters (Å, º) top
Mn1—N12.3006 (12)C1—C21.377 (2)
Mn1—N22.2998 (12)C1—H10.951 (18)
Mn1—O12.3010 (10)C2—C31.379 (2)
Mn1—O22.3766 (10)C2—H20.930 (19)
Mn1—O32.3623 (10)C3—C41.379 (2)
Mn1—O42.3605 (11)C3—H30.925 (19)
Mn1—O62.1486 (12)C4—C51.393 (2)
O1—C111.2573 (16)C4—H40.946 (19)
O2—C121.2554 (16)C5—C61.4849 (19)
C13—O3i1.2450 (17)C6—C71.388 (2)
C14—O4i1.2394 (16)C7—C81.382 (2)
O3—C13ii1.2450 (17)C7—H70.964 (19)
O4—C14ii1.2394 (16)C8—C91.376 (3)
O5—C151.2319 (17)C8—H80.94 (2)
O6—H6A0.85 (2)C9—C101.379 (2)
O6—H6B0.75 (2)C9—H90.96 (2)
O7—H7A0.78 (3)C10—H100.959 (19)
O7—H7B0.79 (3)C11—C121.4494 (18)
N1—C11.3395 (19)C12—C131.4592 (17)
N1—C51.3438 (18)C13—C141.459 (2)
N2—C61.3456 (17)C14—C151.4765 (18)
N2—C101.3363 (19)C11—C151.4704 (18)
O6—Mn1—N2104.20 (5)C3—C2—H2120.2 (11)
O6—Mn1—N1170.14 (5)C2—C3—C4119.03 (14)
N2—Mn1—N170.67 (4)C2—C3—H3122.5 (13)
O6—Mn1—O191.74 (5)C4—C3—H3118.5 (12)
N2—Mn1—O1143.90 (4)C3—C4—C5119.08 (15)
N1—Mn1—O188.26 (4)C3—C4—H4121.0 (11)
O6—Mn1—O478.71 (4)C5—C4—H4119.9 (11)
N2—Mn1—O474.97 (4)N1—C5—C4121.81 (13)
N1—Mn1—O4107.32 (4)N1—C5—C6115.84 (12)
O1—Mn1—O4140.69 (3)C4—C5—C6122.30 (13)
O6—Mn1—O3110.00 (5)N2—C6—C7121.88 (13)
N2—Mn1—O3126.05 (4)N2—C6—C5115.81 (12)
N1—Mn1—O379.54 (4)C7—C6—C5122.29 (13)
O1—Mn1—O375.43 (3)C8—C7—C6118.94 (15)
O4—Mn1—O372.46 (4)C8—C7—H7120.0 (11)
O6—Mn1—O281.12 (4)C6—C7—H7121.1 (11)
N2—Mn1—O277.09 (4)C9—C8—C7119.11 (15)
N1—Mn1—O289.43 (4)C9—C8—H8120.2 (12)
O1—Mn1—O273.63 (3)C7—C8—H8120.6 (12)
O4—Mn1—O2140.03 (3)C8—C9—C10118.80 (15)
O3—Mn1—O2147.39 (4)C8—C9—H9121.5 (11)
C11—O1—Mn1111.89 (8)C10—C9—H9119.7 (11)
C12—O2—Mn1109.23 (8)N2—C10—C9122.86 (15)
C13ii—O3—Mn1111.23 (9)N2—C10—H10116.1 (12)
C14ii—O4—Mn1111.35 (9)C9—C10—H10121.0 (12)
Mn1—O6—H6A122.7 (14)O1—C11—C12122.36 (12)
Mn1—O6—H6B125.1 (17)O1—C11—C15127.61 (12)
H6A—O6—H6B111 (2)C12—C11—C15110.04 (11)
H7A—O7—H7B109 (3)O2—C12—C11122.86 (11)
C1—N1—C5118.24 (12)O2—C12—C13129.42 (12)
C1—N1—Mn1122.84 (10)C11—C12—C13107.72 (11)
C5—N1—Mn1118.69 (9)O3i—C13—C14122.24 (12)
C10—N2—C6118.34 (12)O3i—C13—C12130.25 (14)
C10—N2—Mn1123.01 (10)C14—C13—C12107.51 (11)
C6—N2—Mn1118.62 (9)O4i—C14—C13122.58 (12)
N1—C1—C2123.01 (15)O4i—C14—C15127.90 (13)
N1—C1—H1115.4 (11)C13—C14—C15109.51 (11)
C2—C1—H1121.4 (11)O5—C15—C11127.67 (12)
C1—C2—C3118.80 (15)O5—C15—C14127.18 (12)
C1—C2—H2121.0 (11)C11—C15—C14105.15 (11)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6A···O70.85 (2)1.90 (2)2.7474 (18)175 (2)
O6—H6B···O1iii0.75 (2)2.21 (2)2.9492 (16)176 (2)
O7—H7A···O2iv0.78 (3)2.24 (3)3.0156 (18)171 (3)
O7—H7B···O5v0.79 (3)2.12 (3)2.9030 (18)178 (3)
C7—H7···O2vi0.964 (19)2.534 (19)3.4715 (19)164.2 (15)
Symmetry codes: (iii) x+1, y1/2, z+3/2; (iv) x+1, y, z+2; (v) x+1, y+1, z+2; (vi) x+2, y, z+2.

Experimental details

(I)(II)
Crystal data
Chemical formula[Mn(C5O5)(C10H8N2)(H2O)]·H2O[Mn(C5O5)(C10H8N2)(H2O)]·H2O
Mr387.21387.21
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)135291
a, b, c (Å)11.3363 (2), 9.3622 (1), 14.4053 (2)11.3911 (2), 9.4023 (1), 14.4361 (2)
β (°) 104.8460 (6) 104.740 (1)
V3)1477.84 (4)1495.26 (3)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.940.93
Crystal size (mm)0.26 × 0.20 × 0.110.50 × 0.17 × 0.13
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Bruker APEX2 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(APEX2; Bruker, 2005)
Multi-scan
(APEX2; Bruker, 2005)
Tmin, Tmax0.790, 0.9040.654, 0.889
No. of measured, independent and
observed [I > 2σ(I)] reflections
33771, 5570, 5142 10311, 3251, 2966
Rint0.0180.016
(sin θ/λ)max1)0.7660.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.064, 0.99 0.024, 0.062, 0.96
No. of reflections55703251
No. of parameters275275
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.50, 0.310.27, 0.26

Computer programs: APEX2 (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 2008), WinGX (Farrugia, 1999).

Selected bond lengths (Å) for (I) top
Mn1—N12.2991 (8)Mn1—O62.1484 (8)
Mn1—N22.2990 (7)O1—C111.2605 (10)
Mn1—O12.2990 (6)O2—C121.2574 (10)
Mn1—O22.3719 (7)C13—O3i1.2484 (11)
Mn1—O32.3508 (7)C14—O4i1.2428 (10)
Mn1—O42.3499 (7)O5—C151.2360 (10)
Symmetry code: (i) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O6—H6A···O70.820 (17)1.919 (18)2.7373 (12)175.0 (17)
O6—H6B···O1ii0.779 (19)2.137 (19)2.9153 (10)177.2 (18)
O7—H7A···O2iii0.80 (2)2.20 (2)2.9838 (11)169.1 (19)
O7—H7B···O5iv0.81 (2)2.06 (2)2.8755 (11)176.8 (19)
C7—H7···O2v0.984 (15)2.487 (15)3.4425 (12)163.8 (12)
Symmetry codes: (ii) x+1, y1/2, z+3/2; (iii) x+1, y, z+2; (iv) x+1, y+1, z+2; (v) x+2, y, z+2.
Selected bond lengths (Å) for (II) top
Mn1—N12.3006 (12)Mn1—O62.1486 (12)
Mn1—N22.2998 (12)O1—C111.2573 (16)
Mn1—O12.3010 (10)O2—C121.2554 (16)
Mn1—O22.3766 (10)C13—O3i1.2450 (17)
Mn1—O32.3623 (10)C14—O4i1.2394 (16)
Mn1—O42.3605 (11)O5—C151.2319 (17)
Symmetry code: (i) x, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O6—H6A···O70.85 (2)1.90 (2)2.7474 (18)175 (2)
O6—H6B···O1ii0.75 (2)2.21 (2)2.9492 (16)176 (2)
O7—H7A···O2iii0.78 (3)2.24 (3)3.0156 (18)171 (3)
O7—H7B···O5iv0.79 (3)2.12 (3)2.9030 (18)178 (3)
C7—H7···O2v0.964 (19)2.534 (19)3.4715 (19)164.2 (15)
Symmetry codes: (ii) x+1, y1/2, z+3/2; (iii) x+1, y, z+2; (iv) x+1, y+1, z+2; (v) x+2, y, z+2.
 

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