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Acta Cryst. (2008). E64, m1462    [ doi:10.1107/S1600536808034016 ]

Bis(N,N-dimethylformamide-[kappa]O)bis(1-methylimidazole-2-carbaldehyde oximato-[kappa]2N,O)manganese(III) perchlorate

F. Wang, J. Zhang, Q. Wang and S. Huang

Abstract top

In the title compound, [Mn(C5H6N3O)2(C3H7NO)]ClO4, the MnIII atom lies on the inversion centre of the centrosymmetric complex cation and has a distorted octahedral coordination geometry, formed by two N atoms and two O atoms from two 1-methylimidazole-2-carbaldehyde oximate ligands and two O atoms from two dimethylformamide ligands. Perchlorate acts as a counterion to balance the charge. The crystal structure of the title compound is stabilized by C-H...O hydrogen-bonding interactions.

Comment top

The metal complexes with the 2-((hydroxyimino)methyl)-1-methylimidazole and 2-((hydroxyimino)methyl)-1-ethylimidazole had some good activities (Miyasaka et al., 2005; Saitoh et al., 2007). Herein, we report the crystal structure of such a novel compound, [Mn(C5H6N3O)2(C3H7NO)](ClO4), (I).

The molecular structure of (I) is shown in Fig.1. The Mn atom lying on the inversion center of the centrosymmetric cation has a distorted octahedral geometry and is coordinated by two N atoms and two O atoms (O3,O4) from two 2-((hydroxyimino)methyl)-1-methylimidazole ligands, which lie in the equatorial plane, with the torsional angle O1—N2—O2—N4 = -2.19°, and two O atoms from two N',N-dimthylformamide molecules occupy the axial sites, which is nearly linear [O3—Mn—O4 = 176.62 (10)°] (Table 1). The distance from Mn to the equatorial plane is 0.0828 (15) Å. O3 and O4 are far away from the equatorial plane, with the mean distance 2.32 Å. As shown in Fig. 2, an organic cation layer is linked to an inorganic anionic layer through a series of C—H···O hydrogen bonding interactions (Table 2). In the structure, there are not π-π interactions.

Related literature top

For related literature, see: Miyasaka et al. (2005); Saitoh et al. (2007).

Experimental top

[Mn(C5H6N3O)2 (C3H7NO)](ClO4) was prepared as followings: to a solution of 2-((Hydroxyimino)methyl)-1-methylimidazole 0.50 g(4 mmol) in DMF(25 mL) and triethylamine (0.05 mL) was added Mn(ClO4)2 (0.724 g, 2.0 mmol). After the mixture was stirred for a one hour, the solution was filtered. The filtrate was kept for several days at ambient temperature, and brown block crystals were obtained.

Refinement top

H atoms on C atoms were placed in geometrically idealized positions and refined in riding model, with C–H = 0.93 or 0.96 Å and Uiso(H) = 1.2 or 1.5Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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
[Figure 1] Fig. 1. The molecular structure of (I), showing ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. The hydrogen-bonding structure of the molecular packing diagram of (I).
Bis(N,N-dimethylformamide-κO)bis(1-methylimidazole-2- carbaldehyde oximato-κ2N,O)manganese(III) perchlorate top
Crystal data top
[Mn(C5H6N3O)2(C3H7NO)]ClO4Z = 2
Mr = 548.84F(000) = 568
Triclinic, P1Dx = 1.546 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6158 (11) ÅCell parameters from 2239 reflections
b = 12.324 (2) Åθ = 2.5–22.4°
c = 12.8600 (16) ŵ = 0.73 mm−1
α = 82.841 (10)°T = 298 K
β = 85.273 (11)°Block, brown
γ = 80.471 (16)°0.23 × 0.20 × 0.10 mm
V = 1178.7 (3) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer		4101 independent reflections
Radiation source: fine-focus sealed tube3191 reflections with I > 2σ(I)
graphiteRint = 0.039
φ and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −8→9
Tmin = 0.850, Tmax = 0.930k = −14→12
9397 measured reflectionsl = −15→15
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0845P)2 + 0.2454P]
where P = (Fo2 + 2Fc2)/3
4101 reflections(Δ/σ)max = 0.002
313 parametersΔρmax = 0.40 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Crystal data top
[Mn(C5H6N3O)2(C3H7NO)]ClO4γ = 80.471 (16)°
Mr = 548.84V = 1178.7 (3) Å3
Triclinic, P1Z = 2
a = 7.6158 (11) ÅMo Kα radiation
b = 12.324 (2) ŵ = 0.73 mm−1
c = 12.8600 (16) ÅT = 298 K
α = 82.841 (10)°0.23 × 0.20 × 0.10 mm
β = 85.273 (11)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		4101 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		3191 reflections with I > 2σ(I)
Tmin = 0.850, Tmax = 0.930Rint = 0.039
9397 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.158Δρmax = 0.40 e Å−3
S = 1.08Δρmin = −0.29 e Å−3
4101 reflectionsAbsolute structure: ?
313 parametersFlack parameter: ?
0 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
Mn10.67156 (7)0.67997 (4)0.75744 (4)0.0366 (2)
C10.3414 (5)0.8512 (4)0.7017 (3)0.0513 (11)
H10.25790.80490.72500.062*
C20.3042 (6)0.9582 (4)0.6627 (3)0.0579 (12)
H20.19120.99890.65370.070*
C30.5955 (6)0.9116 (3)0.6626 (3)0.0446 (10)
C40.4845 (7)1.1121 (3)0.5958 (4)0.0667 (14)
H4A0.52571.14810.64910.100*
H4B0.37191.15210.57420.100*
H4C0.56991.11040.53660.100*
C50.7840 (6)0.9159 (4)0.6449 (3)0.0529 (11)
H50.81460.98040.60760.063*
C60.9974 (5)0.5219 (3)0.8403 (3)0.0389 (9)
H61.08180.56460.80960.047*
C71.0311 (5)0.4261 (3)0.9042 (3)0.0415 (9)
H71.14250.39120.92510.050*
C80.7428 (5)0.4639 (3)0.8846 (3)0.0358 (9)
C90.8461 (6)0.2892 (3)1.0015 (3)0.0533 (11)
H9A0.72660.29731.03300.080*
H9B0.92940.27691.05550.080*
H9C0.86600.22720.96120.080*
C100.5576 (5)0.4523 (3)0.8923 (3)0.0462 (10)
H100.52740.38930.93280.055*
C110.6945 (5)0.8367 (3)0.9405 (3)0.0431 (10)
H110.75840.86920.88360.052*
C120.7615 (6)0.9785 (4)1.0387 (3)0.0573 (12)
H12A0.82341.00070.97340.086*
H12B0.84450.95991.09280.086*
H12C0.67111.03841.05700.086*
C130.5781 (6)0.8394 (4)1.1206 (3)0.0624 (13)
H13A0.50950.78681.10200.094*
H13B0.49930.89941.14880.094*
H13C0.65910.80381.17240.094*
C140.7324 (5)0.5286 (4)0.5742 (3)0.0497 (11)
H140.74380.47040.62780.060*
C150.7250 (11)0.5901 (4)0.3915 (4)0.109 (3)
H15A0.64690.65350.41410.164*
H15B0.67480.56410.33500.164*
H15C0.83930.61040.36800.164*
C160.7802 (8)0.3905 (4)0.4514 (4)0.0720 (15)
H16A0.77210.34030.51430.108*
H16B0.89760.37590.41770.108*
H16C0.69350.38050.40470.108*
N10.4629 (5)0.9964 (3)0.6388 (3)0.0507 (9)
N20.5233 (4)0.8215 (3)0.7014 (2)0.0416 (8)
N30.9150 (5)0.8411 (3)0.6746 (3)0.0547 (9)
N40.8164 (4)0.5454 (2)0.8285 (2)0.0355 (7)
N50.8711 (4)0.3896 (3)0.9328 (2)0.0382 (7)
N60.4281 (4)0.5195 (3)0.8494 (3)0.0487 (8)
N70.6785 (4)0.8821 (3)1.0277 (2)0.0429 (8)
N80.7459 (5)0.5038 (3)0.4778 (2)0.0471 (8)
O10.8785 (3)0.7471 (2)0.7320 (2)0.0478 (7)
O20.4629 (3)0.6147 (2)0.7914 (2)0.0508 (7)
O30.6303 (4)0.7528 (2)0.9275 (2)0.0523 (7)
O40.7056 (4)0.6244 (2)0.5996 (2)0.0528 (7)
Cl10.90018 (14)0.19042 (8)0.72382 (8)0.0490 (3)
O51.0504 (6)0.2250 (4)0.7606 (4)0.1166 (16)
O60.7487 (5)0.2738 (3)0.7265 (3)0.0903 (12)
O70.9418 (5)0.1610 (3)0.6206 (2)0.0731 (10)
O80.8620 (5)0.0947 (3)0.7917 (3)0.0839 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0330 (3)0.0354 (4)0.0413 (3)−0.0012 (2)−0.0041 (2)−0.0077 (3)
C10.038 (2)0.058 (3)0.055 (2)0.004 (2)−0.0040 (18)−0.010 (2)
C20.048 (3)0.065 (3)0.053 (2)0.019 (2)−0.007 (2)−0.009 (2)
C30.053 (2)0.041 (2)0.042 (2)0.002 (2)−0.0120 (18)−0.0156 (18)
C40.101 (4)0.037 (3)0.058 (3)0.010 (2)−0.026 (3)−0.006 (2)
C50.060 (3)0.038 (2)0.063 (3)−0.015 (2)−0.010 (2)0.000 (2)
C60.032 (2)0.040 (2)0.045 (2)−0.0012 (17)−0.0015 (16)−0.0104 (18)
C70.030 (2)0.044 (2)0.050 (2)−0.0010 (18)−0.0050 (17)−0.0114 (19)
C80.033 (2)0.032 (2)0.0417 (19)0.0022 (16)−0.0043 (15)−0.0125 (17)
C90.052 (3)0.041 (2)0.061 (3)−0.002 (2)0.000 (2)0.006 (2)
C100.041 (2)0.039 (2)0.061 (2)−0.0122 (19)−0.0018 (19)−0.008 (2)
C110.040 (2)0.046 (3)0.043 (2)0.0006 (19)−0.0045 (16)−0.0091 (19)
C120.066 (3)0.053 (3)0.054 (2)−0.015 (2)−0.007 (2)−0.006 (2)
C130.071 (3)0.075 (3)0.046 (2)−0.026 (3)0.008 (2)−0.014 (2)
C140.051 (2)0.055 (3)0.042 (2)−0.003 (2)−0.0034 (18)−0.008 (2)
C150.214 (8)0.056 (4)0.049 (3)−0.001 (4)0.007 (4)−0.009 (3)
C160.108 (4)0.045 (3)0.059 (3)0.011 (3)−0.011 (3)−0.016 (2)
N10.062 (2)0.042 (2)0.0467 (19)0.0087 (18)−0.0146 (16)−0.0158 (16)
N20.0407 (19)0.040 (2)0.0439 (17)0.0022 (15)−0.0072 (14)−0.0124 (15)
N30.050 (2)0.051 (2)0.065 (2)−0.0155 (19)−0.0046 (17)−0.0029 (19)
N40.0321 (16)0.0362 (18)0.0394 (16)−0.0043 (14)−0.0039 (13)−0.0098 (14)
N50.0349 (17)0.0350 (18)0.0441 (17)−0.0014 (14)−0.0020 (13)−0.0080 (14)
N60.0378 (19)0.047 (2)0.063 (2)−0.0114 (17)−0.0043 (16)−0.0048 (18)
N70.0455 (19)0.047 (2)0.0383 (17)−0.0110 (16)−0.0037 (14)−0.0052 (15)
N80.063 (2)0.039 (2)0.0374 (17)−0.0003 (17)−0.0038 (15)−0.0041 (15)
O10.0418 (16)0.0430 (17)0.0573 (16)−0.0054 (13)−0.0033 (12)−0.0020 (14)
O20.0359 (15)0.0536 (19)0.0620 (17)−0.0066 (13)−0.0089 (13)0.0001 (15)
O30.0614 (19)0.0491 (18)0.0478 (16)−0.0076 (15)−0.0047 (13)−0.0112 (14)
O40.071 (2)0.0438 (17)0.0434 (15)−0.0033 (15)−0.0003 (13)−0.0156 (13)
Cl10.0570 (7)0.0428 (6)0.0473 (5)−0.0056 (5)−0.0017 (4)−0.0092 (5)
O50.098 (3)0.150 (4)0.124 (3)−0.060 (3)−0.011 (3)−0.046 (3)
O60.101 (3)0.067 (2)0.088 (2)0.027 (2)0.002 (2)−0.008 (2)
O70.102 (3)0.062 (2)0.0477 (17)0.0068 (19)0.0013 (17)−0.0089 (15)
O80.113 (3)0.067 (2)0.064 (2)−0.015 (2)0.0083 (19)0.0157 (18)
Geometric parameters (Å, °) top
Mn1—O11.886 (3)C9—H9C0.9600
Mn1—O21.893 (3)C10—N61.292 (5)
Mn1—N41.997 (3)C10—H100.9300
Mn1—N22.002 (3)C11—O31.249 (5)
Mn1—O42.204 (3)C11—N71.304 (5)
Mn1—O32.443 (3)C11—H110.9300
C1—C21.344 (6)C12—N71.461 (5)
C1—N21.372 (5)C12—H12A0.9600
C1—H10.9300C12—H12B0.9600
C2—N11.367 (6)C12—H12C0.9600
C2—H20.9300C13—N71.455 (5)
C3—N21.343 (5)C13—H13A0.9600
C3—N11.352 (5)C13—H13B0.9600
C3—C51.443 (6)C13—H13C0.9600
C4—N11.493 (5)C14—O41.244 (5)
C4—H4A0.9600C14—N81.306 (5)
C4—H4B0.9600C14—H140.9300
C4—H4C0.9600C15—N81.437 (6)
C5—N31.289 (5)C15—H15A0.9600
C5—H50.9300C15—H15B0.9600
C6—C71.351 (5)C15—H15C0.9600
C6—N41.377 (5)C16—N81.455 (5)
C6—H60.9300C16—H16A0.9600
C7—N51.375 (5)C16—H16B0.9600
C7—H70.9300C16—H16C0.9600
C8—N41.335 (5)N3—O11.350 (4)
C8—N51.356 (4)N6—O21.362 (4)
C8—C101.436 (5)Cl1—O61.413 (3)
C9—N51.458 (5)Cl1—O71.416 (3)
C9—H9A0.9600Cl1—O51.420 (4)
C9—H9B0.9600Cl1—O81.433 (3)
O1—Mn1—O2176.56 (11)H12A—C12—H12B109.5
O1—Mn1—N489.45 (12)N7—C12—H12C109.5
O2—Mn1—N489.88 (12)H12A—C12—H12C109.5
O1—Mn1—N290.13 (13)H12B—C12—H12C109.5
O2—Mn1—N290.18 (13)N7—C13—H13A109.5
N4—Mn1—N2173.75 (11)N7—C13—H13B109.5
O1—Mn1—O491.23 (11)H13A—C13—H13B109.5
O2—Mn1—O492.20 (12)N7—C13—H13C109.5
N4—Mn1—O495.89 (11)H13A—C13—H13C109.5
N2—Mn1—O490.35 (11)H13B—C13—H13C109.5
O1—Mn1—O387.46 (11)O4—C14—N8124.9 (4)
O2—Mn1—O389.13 (11)O4—C14—H14117.6
N4—Mn1—O387.21 (10)N8—C14—H14117.6
N2—Mn1—O386.54 (10)N8—C15—H15A109.5
O4—Mn1—O3176.62 (10)N8—C15—H15B109.5
C2—C1—N2108.6 (4)H15A—C15—H15B109.5
C2—C1—H1125.7N8—C15—H15C109.5
N2—C1—H1125.7H15A—C15—H15C109.5
C1—C2—N1107.5 (4)H15B—C15—H15C109.5
C1—C2—H2126.3N8—C16—H16A109.5
N1—C2—H2126.3N8—C16—H16B109.5
N2—C3—N1108.9 (4)H16A—C16—H16B109.5
N2—C3—C5125.5 (4)N8—C16—H16C109.5
N1—C3—C5125.5 (4)H16A—C16—H16C109.5
N1—C4—H4A109.5H16B—C16—H16C109.5
N1—C4—H4B109.5C3—N1—C2107.8 (4)
H4A—C4—H4B109.5C3—N1—C4126.4 (4)
N1—C4—H4C109.5C2—N1—C4125.7 (4)
H4A—C4—H4C109.5C3—N2—C1107.2 (4)
H4B—C4—H4C109.5C3—N2—Mn1122.2 (3)
N3—C5—C3127.9 (4)C1—N2—Mn1130.4 (3)
N3—C5—H5116.1C5—N3—O1118.6 (3)
C3—C5—H5116.1C8—N4—C6107.2 (3)
C7—C6—N4108.3 (3)C8—N4—Mn1122.6 (2)
C7—C6—H6125.9C6—N4—Mn1129.8 (3)
N4—C6—H6125.9C8—N5—C7107.1 (3)
C6—C7—N5107.7 (3)C8—N5—C9127.0 (3)
C6—C7—H7126.2C7—N5—C9125.9 (3)
N5—C7—H7126.2C10—N6—O2119.1 (3)
N4—C8—N5109.7 (3)C11—N7—C13122.0 (4)
N4—C8—C10126.5 (3)C11—N7—C12122.2 (3)
N5—C8—C10123.7 (4)C13—N7—C12115.8 (3)
N5—C9—H9A109.5C14—N8—C15120.2 (4)
N5—C9—H9B109.5C14—N8—C16123.1 (4)
H9A—C9—H9B109.5C15—N8—C16116.7 (3)
N5—C9—H9C109.5N3—O1—Mn1133.5 (2)
H9A—C9—H9C109.5N6—O2—Mn1134.0 (2)
H9B—C9—H9C109.5C11—O3—Mn1120.4 (2)
N6—C10—C8127.3 (4)C14—O4—Mn1129.3 (3)
N6—C10—H10116.3O6—Cl1—O7110.6 (2)
C8—C10—H10116.3O6—Cl1—O5111.4 (3)
O3—C11—N7124.9 (4)O7—Cl1—O5109.5 (2)
O3—C11—H11117.6O6—Cl1—O8108.6 (2)
N7—C11—H11117.6O7—Cl1—O8108.9 (2)
N7—C12—H12A109.5O5—Cl1—O8107.7 (3)
N7—C12—H12B109.5
N2—C1—C2—N1−0.6 (4)O3—Mn1—N4—C881.1 (3)
N2—C3—C5—N3−9.7 (7)O1—Mn1—N4—C6−3.9 (3)
N1—C3—C5—N3173.1 (4)O2—Mn1—N4—C6179.5 (3)
N4—C6—C7—N5−0.2 (4)O4—Mn1—N4—C687.3 (3)
N4—C8—C10—N6−2.3 (6)O3—Mn1—N4—C6−91.4 (3)
N5—C8—C10—N6179.7 (4)N4—C8—N5—C7−0.6 (4)
N2—C3—N1—C2−0.3 (4)C10—C8—N5—C7177.7 (3)
C5—C3—N1—C2177.2 (4)N4—C8—N5—C9179.7 (3)
N2—C3—N1—C4178.6 (3)C10—C8—N5—C9−1.9 (5)
C5—C3—N1—C4−3.8 (6)C6—C7—N5—C80.5 (4)
C1—C2—N1—C30.6 (4)C6—C7—N5—C9−179.9 (3)
C1—C2—N1—C4−178.4 (3)C8—C10—N6—O2−1.7 (6)
N1—C3—N2—C10.0 (4)O3—C11—N7—C13−1.3 (6)
C5—C3—N2—C1−177.6 (3)O3—C11—N7—C12178.2 (4)
N1—C3—N2—Mn1−175.1 (2)O4—C14—N8—C15−1.6 (7)
C5—C3—N2—Mn17.4 (5)O4—C14—N8—C16179.0 (4)
C2—C1—N2—C30.4 (4)C5—N3—O1—Mn116.5 (5)
C2—C1—N2—Mn1174.9 (3)N4—Mn1—O1—N3171.2 (3)
O1—Mn1—N2—C32.4 (3)N2—Mn1—O1—N3−15.0 (3)
O2—Mn1—N2—C3178.9 (3)O3—Mn1—O1—N3−101.5 (3)
O4—Mn1—N2—C3−88.9 (3)C10—N6—O2—Mn1−1.6 (5)
O3—Mn1—N2—C389.8 (3)N4—Mn1—O2—N65.5 (3)
O1—Mn1—N2—C1−171.4 (3)N2—Mn1—O2—N6−168.3 (3)
O2—Mn1—N2—C15.1 (3)O4—Mn1—O2—N6101.4 (3)
O4—Mn1—N2—C197.3 (3)O3—Mn1—O2—N6−81.7 (3)
O3—Mn1—N2—C1−84.0 (3)N7—C11—O3—Mn1179.5 (3)
C3—C5—N3—O1−2.1 (6)O1—Mn1—O3—C1125.0 (3)
N5—C8—N4—C60.5 (4)O2—Mn1—O3—C11−155.5 (3)
C10—C8—N4—C6−177.8 (3)N4—Mn1—O3—C11114.6 (3)
N5—C8—N4—Mn1−173.4 (2)N2—Mn1—O3—C11−65.2 (3)
C10—C8—N4—Mn18.3 (5)N8—C14—O4—Mn1177.9 (3)
C7—C6—N4—C8−0.2 (4)O1—Mn1—O4—C14117.2 (4)
C7—C6—N4—Mn1173.1 (2)O2—Mn1—O4—C14−62.5 (4)
O1—Mn1—N4—C8168.6 (3)N4—Mn1—O4—C1427.6 (4)
O2—Mn1—N4—C8−8.1 (3)N2—Mn1—O4—C14−152.7 (4)
O4—Mn1—N4—C8−100.3 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O7i0.932.543.433 (6)161
C5—H5···O7ii0.932.603.402 (6)145
C12—H12A···O8ii0.962.493.399 (6)157
C13—H13A···O30.962.412.797 (5)103
C13—H13C···O5iii0.962.403.261 (7)150
C14—H14···O60.932.593.477 (6)161
Symmetry codes: (i) x−1, y+1, z; (ii) x, y+1, z; (iii) −x+2, −y+1, −z+2.
Table 1
Selected geometric parameters (Å, °) top
Mn1—O11.886 (3)Mn1—N22.002 (3)
Mn1—O21.893 (3)Mn1—O42.204 (3)
Mn1—N41.997 (3)Mn1—O32.443 (3)
O1—Mn1—O2176.56 (11)N4—Mn1—O495.89 (11)
O1—Mn1—N489.45 (12)N2—Mn1—O490.35 (11)
O2—Mn1—N489.88 (12)O1—Mn1—O387.46 (11)
O1—Mn1—N290.13 (13)O2—Mn1—O389.13 (11)
O2—Mn1—N290.18 (13)N4—Mn1—O387.21 (10)
N4—Mn1—N2173.75 (11)N2—Mn1—O386.54 (10)
O1—Mn1—O491.23 (11)O4—Mn1—O3176.62 (10)
O2—Mn1—O492.20 (12)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O7i0.932.543.433 (6)161
C5—H5···O7ii0.932.603.402 (6)145
C12—H12A···O8ii0.962.493.399 (6)157
C13—H13A···O30.962.412.797 (5)103
C13—H13C···O5iii0.962.403.261 (7)150
C14—H14···O60.932.593.477 (6)161
Symmetry codes: (i) x−1, y+1, z; (ii) x, y+1, z; (iii) −x+2, −y+1, −z+2.
references
References top

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Miyasaka, H., Saitoh, A., Yanagida, S., Kachi-Terajima, C., Sugiura, K. & Yamashita, M. (2005). Inorg. Chim. Acta, 358, 3525–3535.

Saitoh, A., Miyasaka, H., Yamashita, M. & Clerac, R. (2007). J. Mater. Chem. 17, 2002–2012.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.