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Acta Cryst. (2007). E63, m2198-m2199    [ doi:10.1107/S1600536807035076 ]

(Dihydroxyglyoxime-[kappa]2N,N')bis(1,10-phenanthroline-[kappa]2N,N')manganese(II) dinitrate dihydrate

T. Liu, Z.-W. Wang, Y.-X. Wang and Z.-P. Xie

Abstract top

In the cation of the title compound, [Mn(C12H8N2)2(C2H4N2O4)](NO3)2·2H2O, the Mn atom has a distorted octahedral coordination formed by six N atoms from one dihydroxyglyoxime and two 1,10-phenanthroline ligands. In the crystal structure, the components are linked into a three-dimensional framework by O-H...O, C-H...O, C-H...N and O-H...N hydrogen bonds and [pi]-[pi] stacking interactions, with a centroid-centroid distance of 3.580 (2) Å (symmetry code: 1 - x, 2 - y, -z).

Comment top

The crystal structure of bis(1,10-phenanthroline-N,N')(dihydroxy glyoxime) copper(II) dinitrate dihydrate, (II), and bis(1,10-phenanthroline-N,N') (dihydroxy glyoxime) cobalt(II) dinitrate dihydrate, (III), has previously been reported (Liu et al., 2007). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with that of (II) and (III). We report herein the crystal structure of (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The six N atoms of one dihydroxy glyoxime and two 1,10-phenanthroline (phen) ligands are coordinated to the Mn atom, in a distorted octahedral arrangement (Table 1). The dihydroxy glyoxime and two phen ligands are each planar and the phen ligands are nearly perpendicular to each other, with a dihedral angle of 86.94 (7)°, as in (II) and (III).

In the crystal structure, the molecules are linked into a three-dimensional framework (Fig. 2) by O—H···O, C—H···O, C—H···N and O—H···N hydrogen bonds (Table 2). There are π-π stacking interactions between adjacent phen ligands with centroid-centroid distance of 3.580 (2) Å (symmetry code: 1 - x, 2 - y, -z). These π-π stacking interactions and hydrogen bonds lead to a supramolecular network structure (Fig. 2), as in (II) and (III). The three compounds, (I), (II) and (III), are isostructural.

Related literature top

For a related structure, see: Liu et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

Manganese dinitrate hexahydrate (144 mg, 0.5 mmol), phen (198 mg, 1 mmol) and dihydroxy glyoxime (120 mg, 1 mmol) were dissolved in ethanol (15 ml). The mixture was heated for 5 h under reflux with stirring. It was then filtered to give a clear solution, into which diethyl ether vapour was allowed to condense in a closed vessel. After being allowed to stand for a few days at room temperature, some colourless single crystals suitable for X-ray diffraction analysis precipitated.

Refinement top

H atoms of the water molecules were located in a difference synthesis and refined freely. The remaining H atoms were positioned geometrically, with O—H = 0.82 Å (for OH) and C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C, O), where x = 1.2 for aromatic H atoms and x = 1.5 for hydroxyl H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Solvent molecules have been omitted for clarity.
[Figure 2] Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.
(Dihydroxyglyoxime-κ2N,N')bis(1,10-phenanthroline-\ κ2N,N')manganese(II) dinitrate dihydrate top
Crystal data top
[Mn(C12H8N2)2(C2H4N2O4)](NO3)2·2H2OF(000) = 1428
Mr = 695.47Dx = 1.535 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5592 reflections
a = 13.913 (2) Åθ = 2.1–25.0°
b = 11.998 (5) ŵ = 0.52 mm−1
c = 18.131 (3) ÅT = 273 K
β = 96.228 (4)°Prism, colourless
V = 3008.6 (14) Å30.30 × 0.23 × 0.18 mm
Z = 4
Data collection top
Bruker APEX II area-detector
diffractometer		6179 independent reflections
Radiation source: fine-focus sealed tube3132 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 26.7°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −17→17
Tmin = 0.861, Tmax = 0.912k = −15→15
20095 measured reflectionsl = −22→22
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0806P)2]
where P = (Fo2 + 2Fc2)/3
6179 reflections(Δ/σ)max = 0.001
444 parametersΔρmax = 0.65 e Å−3
12 restraintsΔρmin = −0.49 e Å−3
Crystal data top
[Mn(C12H8N2)2(C2H4N2O4)](NO3)2·2H2OV = 3008.6 (14) Å3
Mr = 695.47Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.913 (2) ŵ = 0.52 mm−1
b = 11.998 (5) ÅT = 273 K
c = 18.131 (3) Å0.30 × 0.23 × 0.18 mm
β = 96.228 (4)°
Data collection top
Bruker APEX II area-detector
diffractometer		6179 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3132 reflections with I > 2σ(I)
Tmin = 0.861, Tmax = 0.912Rint = 0.041
20095 measured reflectionsθmax = 26.7°
Refinement top
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.166Δρmax = 0.65 e Å−3
S = 0.99Δρmin = −0.49 e Å−3
6179 reflectionsAbsolute structure: ?
444 parametersFlack parameter: ?
12 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
Mn10.77582 (4)0.75577 (4)0.03825 (3)0.03420 (19)
O10.7959 (2)0.9968 (2)0.04742 (16)0.0605 (8)
H1A0.80190.99770.00290.091*
O20.8357 (2)0.6023 (3)0.14815 (18)0.0683 (9)
H2A0.81500.59690.18870.102*
O30.9306 (4)0.7550 (5)0.2469 (3)0.1472 (19)
H3A0.98900.76410.24670.221*
O40.9029 (4)0.9960 (4)0.1826 (4)0.155 (2)
H4A0.95020.98090.21200.233*
O50.7738 (3)0.1306 (3)0.9096 (2)0.0962 (13)
O60.8934 (2)0.0146 (3)0.9287 (2)0.0783 (10)
O70.8897 (4)0.1357 (4)0.8427 (3)0.1356 (19)
O80.7404 (6)0.8835 (8)0.2850 (4)0.219 (4)
O90.6159 (6)0.8842 (6)0.3345 (4)0.209 (3)
O100.6416 (8)1.0073 (6)0.2609 (6)0.388 (11)
O110.5552 (13)0.4230 (13)0.1434 (9)0.574 (14)
O120.695 (2)0.3357 (18)0.2000 (11)0.64 (2)
N10.6533 (2)0.7803 (3)0.0767 (2)0.0492 (9)
N20.7067 (2)0.8181 (3)−0.05277 (19)0.0453 (9)
N30.7384 (2)0.6057 (3)0.00436 (19)0.0495 (9)
N40.8938 (2)0.7246 (3)−0.00697 (18)0.0459 (9)
N50.8376 (2)0.7049 (3)0.1295 (2)0.0490 (9)
N60.8222 (2)0.8935 (3)0.0762 (2)0.0473 (9)
N70.8510 (3)0.0927 (4)0.8919 (3)0.0713 (12)
N80.6670 (6)0.9299 (9)0.2896 (5)0.155 (4)
C10.6298 (3)0.7618 (4)0.1438 (3)0.0601 (12)
H10.67690.73530.17980.072*
C20.5368 (4)0.7804 (4)0.1633 (3)0.0707 (14)
H20.52360.76780.21180.085*
C30.4665 (3)0.8164 (4)0.1125 (3)0.0666 (14)
H30.40420.82700.12530.080*
C40.4872 (3)0.8374 (3)0.0413 (3)0.0570 (12)
C50.4199 (3)0.8792 (4)−0.0160 (3)0.0690 (14)
H50.35610.8914−0.00740.083*
C60.4483 (4)0.9013 (4)−0.0837 (3)0.0729 (15)
H60.40350.9295−0.12080.088*
C70.5460 (3)0.8824 (4)−0.0996 (3)0.0575 (12)
C80.5799 (4)0.9054 (4)−0.1654 (3)0.0720 (15)
H80.53820.9344−0.20430.086*
C90.6765 (4)0.8862 (4)−0.1753 (3)0.0742 (15)
H90.69990.9041−0.22000.089*
C100.7378 (3)0.8397 (3)−0.1172 (3)0.0562 (12)
H100.80160.8238−0.12420.067*
C110.6126 (3)0.8395 (3)−0.0444 (2)0.0468 (10)
C120.5836 (3)0.8180 (3)0.0252 (2)0.0459 (10)
C130.6605 (3)0.5457 (4)0.0147 (3)0.0667 (13)
H130.61400.57550.04220.080*
C140.6478 (4)0.4399 (4)−0.0147 (3)0.0818 (17)
H140.59310.3993−0.00650.098*
C150.7135 (4)0.3950 (4)−0.0549 (3)0.0762 (15)
H150.70360.3244−0.07550.091*
C160.7964 (3)0.4549 (3)−0.0657 (2)0.0542 (12)
C170.8730 (4)0.4158 (4)−0.1057 (3)0.0659 (14)
H170.86700.3463−0.12850.079*
C180.9528 (4)0.4755 (4)−0.1116 (2)0.0607 (13)
H181.00100.4465−0.13770.073*
C190.9653 (3)0.5827 (4)−0.0786 (2)0.0488 (10)
C201.0468 (3)0.6503 (4)−0.0802 (2)0.0591 (12)
H201.09870.6262−0.10430.071*
C211.0498 (3)0.7506 (4)−0.0466 (2)0.0591 (12)
H211.10400.7957−0.04780.071*
C220.9729 (3)0.7873 (3)−0.0101 (2)0.0516 (11)
H220.97650.85690.01270.062*
C230.8909 (3)0.6235 (3)−0.0409 (2)0.0461 (10)
C240.8064 (3)0.5585 (3)−0.0346 (2)0.0463 (10)
C250.8807 (3)0.7818 (4)0.1722 (2)0.0509 (11)
C260.8680 (3)0.8923 (4)0.1413 (3)0.0533 (11)
H11A0.511 (3)0.401 (3)0.111 (3)0.570 (13)*
H12A0.674 (8)0.286 (4)0.228 (5)0.64 (3)*
H11B0.5599 (19)0.4908 (14)0.1538 (16)0.573 (7)*
H12B0.731 (2)0.307 (3)0.1701 (18)0.642 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0323 (3)0.0334 (3)0.0362 (3)0.0025 (3)0.0005 (2)−0.0023 (3)
O10.075 (2)0.0436 (17)0.061 (2)0.0081 (14)−0.0009 (18)0.0001 (15)
O20.075 (2)0.063 (2)0.066 (2)0.0010 (16)0.0004 (18)0.0183 (17)
O30.143 (4)0.182 (5)0.106 (4)0.004 (4)−0.031 (3)0.020 (3)
O40.175 (6)0.125 (4)0.155 (5)−0.013 (3)−0.026 (4)−0.042 (4)
O50.067 (2)0.104 (3)0.120 (3)0.020 (2)0.021 (2)0.006 (2)
O60.078 (2)0.059 (2)0.096 (3)0.0090 (18)0.003 (2)0.018 (2)
O70.134 (4)0.147 (4)0.136 (4)0.028 (3)0.058 (3)0.064 (3)
O80.168 (6)0.293 (10)0.204 (8)−0.064 (7)0.058 (6)−0.083 (6)
O90.229 (9)0.218 (8)0.175 (7)0.002 (6)0.000 (6)−0.022 (6)
O100.55 (2)0.142 (6)0.380 (14)−0.070 (8)−0.355 (14)0.128 (7)
O110.55 (3)0.76 (3)0.48 (3)0.09 (3)0.39 (2)0.16 (2)
O120.56 (3)0.94 (5)0.40 (3)0.04 (3)−0.09 (2)−0.40 (3)
N10.048 (2)0.044 (2)0.055 (2)0.0009 (15)0.0006 (18)−0.0012 (17)
N20.052 (2)0.039 (2)0.044 (2)0.0024 (15)0.0001 (17)−0.0074 (16)
N30.046 (2)0.048 (2)0.054 (2)−0.0017 (17)0.0016 (17)−0.0013 (18)
N40.046 (2)0.040 (2)0.050 (2)0.0034 (15)−0.0021 (16)−0.0018 (16)
N50.046 (2)0.047 (2)0.054 (2)0.0020 (16)0.0027 (17)0.0055 (19)
N60.045 (2)0.046 (2)0.050 (2)0.0041 (16)0.0028 (17)0.0006 (17)
N70.063 (3)0.069 (3)0.082 (4)−0.006 (2)0.010 (2)0.010 (3)
N80.108 (6)0.245 (12)0.116 (7)−0.070 (7)0.031 (5)−0.083 (7)
C10.055 (3)0.074 (3)0.052 (3)0.007 (2)0.007 (2)0.009 (3)
C20.061 (3)0.082 (4)0.070 (4)0.006 (3)0.013 (3)−0.003 (3)
C30.049 (3)0.068 (3)0.086 (4)−0.004 (2)0.022 (3)−0.012 (3)
C40.044 (3)0.046 (3)0.079 (4)0.002 (2)−0.002 (2)−0.010 (2)
C50.048 (3)0.067 (3)0.090 (4)0.007 (2)−0.003 (3)−0.006 (3)
C60.061 (3)0.061 (3)0.090 (4)0.012 (2)−0.022 (3)−0.004 (3)
C70.061 (3)0.052 (3)0.057 (3)0.005 (2)−0.009 (2)−0.003 (2)
C80.077 (4)0.064 (3)0.069 (4)0.012 (3)−0.019 (3)−0.002 (3)
C90.108 (5)0.058 (3)0.053 (3)0.002 (3)−0.005 (3)−0.006 (3)
C100.070 (3)0.053 (3)0.045 (3)0.002 (2)0.002 (2)−0.003 (2)
C110.047 (3)0.038 (2)0.052 (3)0.0021 (19)−0.005 (2)−0.001 (2)
C120.042 (2)0.038 (2)0.056 (3)0.0024 (18)0.000 (2)−0.003 (2)
C130.055 (3)0.052 (3)0.094 (4)−0.009 (2)0.010 (3)−0.004 (3)
C140.066 (3)0.054 (3)0.125 (5)−0.015 (3)0.012 (3)−0.009 (3)
C150.078 (4)0.047 (3)0.101 (5)−0.006 (3)−0.002 (3)−0.015 (3)
C160.064 (3)0.039 (2)0.057 (3)0.005 (2)−0.005 (2)−0.003 (2)
C170.093 (4)0.053 (3)0.049 (3)0.018 (3)−0.005 (3)−0.007 (2)
C180.077 (3)0.058 (3)0.046 (3)0.021 (3)0.002 (2)−0.006 (2)
C190.050 (3)0.054 (3)0.041 (3)0.013 (2)0.000 (2)0.004 (2)
C200.054 (3)0.073 (3)0.052 (3)0.015 (2)0.012 (2)0.003 (3)
C210.048 (3)0.068 (3)0.062 (3)−0.001 (2)0.006 (2)0.003 (3)
C220.044 (3)0.051 (2)0.059 (3)0.000 (2)0.002 (2)−0.003 (2)
C230.047 (2)0.046 (2)0.043 (3)0.007 (2)−0.0049 (19)0.003 (2)
C240.053 (3)0.042 (2)0.042 (3)0.009 (2)−0.002 (2)0.000 (2)
C250.045 (2)0.060 (3)0.046 (3)0.004 (2)−0.001 (2)0.002 (2)
C260.052 (3)0.057 (3)0.051 (3)−0.002 (2)0.001 (2)−0.011 (2)
Geometric parameters (Å, º) top
Mn1—N11.933 (3)C3—C41.376 (6)
Mn1—N21.966 (3)C3—H30.9300
Mn1—N31.955 (3)C4—C51.414 (6)
Mn1—N41.949 (3)C4—C121.421 (5)
Mn1—N51.881 (4)C5—C61.355 (7)
Mn1—N61.877 (3)C5—H50.9300
O1—N61.378 (4)C6—C71.437 (7)
O1—H1A0.8200C6—H60.9300
O2—N51.278 (4)C7—C81.359 (6)
O2—H2A0.8200C7—C111.387 (6)
O3—C251.488 (6)C8—C91.395 (7)
O3—H3A0.8200C8—H80.9300
O4—C261.505 (6)C9—C101.398 (6)
O4—H4A0.8200C9—H90.9300
O5—N71.240 (5)C10—H100.9300
O6—N71.259 (5)C11—C121.390 (6)
O7—N71.207 (5)C13—C141.380 (6)
O8—N81.174 (9)C13—H130.9300
O9—N81.262 (8)C14—C151.342 (6)
O10—N81.104 (11)C14—H140.9300
O11—H11A0.85 (5)C15—C161.390 (6)
O11—H11B0.836 (10)C15—H150.9300
O12—H12A0.86 (8)C16—C241.366 (5)
O12—H12B0.85 (4)C16—C171.432 (6)
N1—C11.313 (5)C17—C181.335 (6)
N1—C121.349 (5)C17—H170.9300
N2—C101.315 (5)C18—C191.420 (6)
N2—C111.358 (5)C18—H180.9300
N3—C131.331 (5)C19—C231.390 (5)
N3—C241.363 (5)C19—C201.397 (6)
N4—C221.340 (5)C20—C211.348 (6)
N4—C231.358 (5)C20—H200.9300
N5—C251.308 (5)C21—C221.389 (5)
N6—C261.280 (5)C21—H210.9300
C1—C21.395 (6)C22—H220.9300
C1—H10.9300C23—C241.427 (5)
C2—C31.339 (7)C25—C261.443 (6)
C2—H20.9300
N1—Mn1—N282.79 (15)C7—C6—H6119.2
N1—Mn1—N392.23 (14)C8—C7—C11116.2 (5)
N1—Mn1—N4175.49 (14)C8—C7—C6124.7 (5)
N1—Mn1—N593.95 (15)C11—C7—C6119.1 (5)
N1—Mn1—N690.86 (14)C7—C8—C9120.7 (5)
N2—Mn1—N389.86 (13)C7—C8—H8119.6
N2—Mn1—N494.46 (14)C9—C8—H8119.6
N2—Mn1—N5175.53 (14)C8—C9—C10119.1 (5)
N2—Mn1—N695.16 (14)C8—C9—H9120.4
N3—Mn1—N484.17 (14)C10—C9—H9120.4
N3—Mn1—N593.32 (15)N2—C10—C9121.0 (5)
N3—Mn1—N6174.40 (14)N2—C10—H10119.5
N4—Mn1—N588.99 (14)C9—C10—H10119.5
N4—Mn1—N692.95 (13)N2—C11—C7124.4 (4)
N5—Mn1—N681.81 (15)N2—C11—C12116.4 (4)
N6—O1—H1A109.5C7—C11—C12119.1 (4)
N5—O2—H2A109.5N1—C12—C11115.6 (4)
C25—O3—H3A109.5N1—C12—C4122.5 (4)
C26—O4—H4A109.5C11—C12—C4121.9 (4)
H11A—O11—H11B120 (3)N3—C13—C14121.0 (5)
H12A—O12—H12B111 (7)N3—C13—H13119.5
C1—N1—C12117.7 (4)C14—C13—H13119.5
C1—N1—Mn1128.8 (3)C15—C14—C13120.9 (5)
C12—N1—Mn1113.4 (3)C15—C14—H14119.6
C10—N2—C11118.5 (4)C13—C14—H14119.6
C10—N2—Mn1130.0 (3)C14—C15—C16119.5 (5)
C11—N2—Mn1111.6 (3)C14—C15—H15120.2
C13—N3—C24118.0 (4)C16—C15—H15120.2
C13—N3—Mn1130.3 (3)C24—C16—C15117.5 (4)
C24—N3—Mn1111.7 (3)C24—C16—C17117.3 (4)
C22—N4—C23117.8 (4)C15—C16—C17125.2 (4)
C22—N4—Mn1130.0 (3)C18—C17—C16122.3 (4)
C23—N4—Mn1112.1 (3)C18—C17—H17118.8
O2—N5—C25122.9 (4)C16—C17—H17118.8
O2—N5—Mn1121.7 (3)C17—C18—C19121.2 (4)
C25—N5—Mn1115.4 (3)C17—C18—H18119.4
C26—N6—O1116.4 (3)C19—C18—H18119.4
C26—N6—Mn1116.5 (3)C23—C19—C20117.0 (4)
O1—N6—Mn1125.9 (3)C23—C19—C18117.5 (4)
O7—N7—O5120.2 (5)C20—C19—C18125.5 (4)
O7—N7—O6119.3 (5)C21—C20—C19119.7 (4)
O5—N7—O6120.3 (5)C21—C20—H20120.1
O10—N8—O8127.0 (11)C19—C20—H20120.1
O10—N8—O9119.7 (11)C20—C21—C22120.7 (4)
O8—N8—O9113.3 (11)C20—C21—H21119.7
N1—C1—C2122.6 (4)C22—C21—H21119.7
N1—C1—H1118.7N4—C22—C21121.4 (4)
C2—C1—H1118.7N4—C22—H22119.3
C3—C2—C1120.4 (5)C21—C22—H22119.3
C3—C2—H2119.8N4—C23—C19123.4 (4)
C1—C2—H2119.8N4—C23—C24115.9 (4)
C2—C3—C4119.5 (5)C19—C23—C24120.7 (4)
C2—C3—H3120.3N3—C24—C16123.1 (4)
C4—C3—H3120.3N3—C24—C23116.0 (4)
C3—C4—C5124.4 (5)C16—C24—C23120.9 (4)
C3—C4—C12117.4 (4)N5—C25—C26112.9 (4)
C5—C4—C12118.2 (5)N5—C25—O3121.7 (4)
C6—C5—C4120.0 (5)C26—C25—O3125.2 (4)
C6—C5—H5120.0N6—C26—C25113.3 (4)
C4—C5—H5120.0N6—C26—O4123.5 (4)
C5—C6—C7121.7 (5)C25—C26—O4123.2 (4)
C5—C6—H6119.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N20.822.672.991 (4)105
O2—H2A···O30.822.632.791 (7)93
C1—H1···N50.932.533.009 (5)112
C13—H13···N10.932.583.037 (6)111
C22—H22···N60.932.583.030 (5)110
O1—H1A···O5i0.822.332.958 (5)134
O1—H1A···O6i0.821.962.674 (5)145
C3—H3···O5ii0.932.543.385 (6)151
C5—H5···O1iii0.932.543.344 (6)145
C18—H18···O2iv0.932.373.225 (6)152
C22—H22···O6v0.932.523.269 (6)137
C15—H15···O5vi0.932.553.361 (6)146
Symmetry codes: (i) x, y+1, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z; (v) −x+2, −y+1, −z+1; (vi) x, y, z−1.
Selected geometric parameters (Å, º) top
Mn1—N11.933 (3)Mn1—N41.949 (3)
Mn1—N21.966 (3)Mn1—N51.881 (4)
Mn1—N31.955 (3)Mn1—N61.877 (3)
N1—Mn1—N282.79 (15)N2—Mn1—N695.16 (14)
N1—Mn1—N392.23 (14)N3—Mn1—N484.17 (14)
N1—Mn1—N4175.49 (14)N3—Mn1—N593.32 (15)
N1—Mn1—N593.95 (15)N3—Mn1—N6174.40 (14)
N1—Mn1—N690.86 (14)N4—Mn1—N588.99 (14)
N2—Mn1—N389.86 (13)N4—Mn1—N692.95 (13)
N2—Mn1—N494.46 (14)N5—Mn1—N681.81 (15)
N2—Mn1—N5175.53 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N20.822.672.991 (4)105
O2—H2A···O30.822.632.791 (7)93
C1—H1···N50.932.533.009 (5)112
C13—H13···N10.932.583.037 (6)111
C22—H22···N60.932.583.030 (5)110
O1—H1A···O5i0.822.332.958 (5)134
O1—H1A···O6i0.821.962.674 (5)145
C3—H3···O5ii0.932.543.385 (6)151
C5—H5···O1iii0.932.543.344 (6)145
C18—H18···O2iv0.932.373.225 (6)152
C22—H22···O6v0.932.523.269 (6)137
C15—H15···O5vi0.932.553.361 (6)146
Symmetry codes: (i) x, y+1, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z; (iv) −x+2, −y+1, −z; (v) −x+2, −y+1, −z+1; (vi) x, y, z−1.
Acknowledgements top

We thank the Youth Program of Jinggangshan University for financial support of this work.

references
References top

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