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Acta Cryst. (2007). E63, m3055    [ doi:10.1107/S1600536807054517 ]

Aquachlorido[4,4'-dimethyl-N,N'-(o-phenylene)bis(pyridine-2-carboxamidato)]manganese(III) dimethylformamide solvate

L. Yang, Z. Jiang and X.-G. Zhou

Abstract top

In the title compound, [Mn(C20H16N4O2)Cl(H2O)]·C3H7NO, or [Mn(bmpb)Cl(H2O)]·DMF [H2bmpb = 1,2-bis(4'-methylpyridine-2'-carboxamido)benzene and DMF is dimethylformamide], the MnIII ion is six-coordinate in the form of a distorted octahedron with two pyridine and two deprotonated amide N atoms in the equatorial plane, while the two axial sites are occupied by a chloride ion and an O atom. The structure displays O-H...O hydrogen bonds.

Comment top

Manganese complexes are involved in numerous biological redox reactions performed by metalloenzymes (Larson et al., 1992). The carboxamide [–C(O)NH–] group, ubiquitous throughout nature in the primary structure of proteins, is an important ligand for coordination chemists. On the other hand, pyridine carboxamides, a burgeoning class of multidentate ligands containing this linkage, are available from condensation reactions. Here we describe the coordination chemistry of manganese(III) with a tetradentate pyridine carboxamide ligand prepared from 4-methylpyridine carboxylic acid and 1,2-diaminobenzene.

The crystal structure of the title compound is represented in Figure 1. A s shown in Fig. 1, the mononuclear MnIII ion is six-coordinated, forming a distorted octahedron with two pyridine and two deprotonated amide N atoms in the equatorial plane, while the two axial sites are occupied by Cl ion and O atom provided by a water molecule. The Mn—N(amide) distances of ca 1.92 Å are significantly shorter than the Mn—N(pyridine) distances of ca 2.07 Å, both of which are appreciably shorter than the Mn—N distances found in related Mn—N4 complexes such as cis-[MnII(mep)Cl2] and [MnIII(mpp)Cl(OH2)](ClO4) [mep = N,N'-dimethyl-N,N'- bis(2-pyridylmethyl)ethane-1,2-diamino, mpp = N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)propane-1,2-diamino] (Hureau et al., 2005). The Mn—N(amide) and Mn—N(pyridine) distances are also comparable to those of [Mn(bpc)Cl(DMF)] [H2bpc =1,2- bis(2- pyridinecarboxamido)-4,5-dichlorobenzene] (Liang et al., 2007). The Mn—Cl distance at 2.463 Å is very similar to what is observed for [(mpp)MnCl(OH2)](ClO4)(Hureau et al., 2005). However, The Mn—O distance (ca 2.27 Å) in the title compound is longer than the corresponding Mn—O distances (ca 2.19 Å) in [(mpp)MnCl(OH2)](ClO4) (Hureau et al., 2005), due to the distinctive hydrogen-bond effect.

Related literature top

The complex was prepared by the reaction of Mn(CH3COO)3·2H2O and H2bmpb in DMF in the presence of LiCl (Ray et al., 1993). For other related literature, see: Larson et al. (1992); Liang et al. (2007); Hureau et al. (2005).

Experimental top

The title complex was prepared in a manner similar to the literature by the reaction of manganese(III) acetate and H2bmpb in DMF in the presence of triethylamine (Ray et al., 1993). Single crystals suitable for X-ray analysis were obtained by slow diffusion of diethyl ether into a DMF solution of the complex. Selected IR data (KBr, cm−1): 2950 (m), 1630 (amide I band, s), 1600(amide II band, s), 1480 (s), 1350 (s), 1165(s), 1020 (m), 850 (m). Analysis calculated for C23H25ClMnN5O4: C 52.53, H 4.79, Cl 6.74, N 13.32, %; found:C 52.87, H 4.32, Cl 6.78 N 12.58%. MS (FAB): 399 ([Mn(bmpb)]+).

Refinement top

All H atoms were fixed geometrically and treated as riding on their parent atoms with O—H =0.86 Å, Caromatic—H = 0.93 Å and Cmethyl—H = 0.96 Å with Uiso(H)= 1.2Ueq(C,O) or Uiso(H) = 1.5Ueq(Cmethyl).

Computing details top

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

Figures top
[Figure 1] Fig. 1. A view of anion of the title complex with displacement ellipsoids drawn at the 30% propability level. The dashed line depicts an intermolecular hydrogen bond.
Aquachlorido[4,4'-dimethyl-N,N'-(o-phenylene)bis(pyridine-2- carboxamidato)]manganese(III) dimethylformamide solvate top
Crystal data top
[Mn(C20H16N4O2)Cl(H2O)]·C3H7NOF000 = 1088
Mr = 525.87Dx = 1.392 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
a = 11.7182 (15) ÅCell parameters from 4879 reflections
b = 15.503 (2) Åθ = 1–27.5º
c = 14.0158 (19) ŵ = 0.67 mm−1
β = 99.892 (3)ºT = 294 (2) K
V = 2508.4 (6) Å3Prism, black
Z = 40.24 × 0.16 × 0.12 mm
Data collection top
Bruker CCD area-detector
diffractometer		5805 independent reflections
Radiation source: fine-focus sealed tube2687 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.087
T = 294(2) Kθmax = 27.6º
phi and ω scansθmin = 2.0º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→15
Tmin = 0.856, Tmax = 0.924k = −20→17
16639 measured reflectionsl = −18→17
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.178  w = 1/[σ2(Fo2) + (0.075P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
5805 reflectionsΔρmax = 0.57 e Å−3
310 parametersΔρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Mn(C20H16N4O2)Cl(H2O)]·C3H7NOV = 2508.4 (6) Å3
Mr = 525.87Z = 4
Monoclinic, P21/cMo Kα
a = 11.7182 (15) ŵ = 0.67 mm−1
b = 15.503 (2) ÅT = 294 (2) K
c = 14.0158 (19) Å0.24 × 0.16 × 0.12 mm
β = 99.892 (3)º
Data collection top
Bruker CCD area-detector
diffractometer		5805 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2687 reflections with I > 2σ(I)
Tmin = 0.856, Tmax = 0.924Rint = 0.087
16639 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.059310 parameters
wR(F2) = 0.178H-atom parameters constrained
S = 1.02Δρmax = 0.57 e Å−3
5805 reflectionsΔρmin = −0.41 e Å−3
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 > 2sigma(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
Mn10.29430 (4)0.02350 (4)0.62328 (4)0.04348 (16)
Cl10.42626 (8)0.13481 (7)0.57974 (8)0.0620 (3)
O1−0.0071 (2)0.13130 (16)0.49219 (18)0.0549 (7)
O1W0.2130 (2)−0.10901 (18)0.6296 (2)0.0699 (9)
H1WA0.1476−0.12600.59810.084*
H1WB0.2234−0.13600.68410.084*
O20.3918 (3)0.0425 (2)0.9130 (2)0.0834 (10)
N10.1508 (2)0.08875 (18)0.6048 (2)0.0427 (7)
N20.2379 (2)0.00161 (18)0.4774 (2)0.0452 (8)
N30.4375 (2)−0.04517 (18)0.6902 (2)0.0453 (8)
N40.2958 (2)0.05783 (19)0.7554 (2)0.0463 (8)
C10.1261 (3)0.1318 (2)0.6878 (3)0.0433 (9)
C20.2085 (3)0.1156 (2)0.7712 (3)0.0463 (9)
C30.1998 (3)0.1578 (3)0.8564 (3)0.0620 (12)
H3A0.25560.14930.91130.074*
C40.1080 (4)0.2124 (3)0.8596 (3)0.0701 (13)
H4A0.10170.23990.91740.084*
C50.0266 (4)0.2269 (3)0.7800 (3)0.0668 (13)
H5A−0.03460.26410.78410.080*
C60.0334 (3)0.1872 (2)0.6927 (3)0.0533 (11)
H6A−0.02280.19730.63830.064*
C70.0855 (3)0.0923 (2)0.5156 (3)0.0440 (9)
C80.1376 (3)0.0425 (2)0.4426 (3)0.0435 (9)
C90.0869 (3)0.0375 (2)0.3471 (3)0.0537 (11)
H9A0.01730.06600.32590.064*
C100.1382 (4)−0.0096 (3)0.2818 (3)0.0567 (11)
C110.2401 (4)−0.0520 (3)0.3179 (3)0.0646 (12)
H11A0.2769−0.08530.27690.078*
C120.2873 (3)−0.0450 (3)0.4147 (3)0.0582 (11)
H12A0.3563−0.07370.43760.070*
C130.3800 (3)0.0274 (3)0.8262 (3)0.0517 (10)
C140.4618 (3)−0.0318 (2)0.7858 (3)0.0455 (9)
C150.5545 (3)−0.0706 (2)0.8444 (3)0.0500 (10)
H15A0.5691−0.05960.91060.060*
C160.6255 (3)−0.1261 (2)0.8037 (3)0.0507 (10)
C170.5988 (3)−0.1395 (3)0.7056 (3)0.0585 (11)
H17A0.6440−0.17670.67570.070*
C180.5048 (3)−0.0981 (3)0.6506 (3)0.0573 (11)
H18A0.4887−0.10770.58410.069*
C190.0836 (4)−0.0150 (3)0.1775 (3)0.0816 (15)
H19A0.07640.04190.15000.122*
H19B0.0082−0.04070.17210.122*
H19C0.1311−0.04970.14320.122*
C200.7271 (3)−0.1707 (3)0.8662 (3)0.0672 (13)
H20A0.7838−0.18590.82710.101*
H20B0.7005−0.22200.89390.101*
H20C0.7614−0.13250.91700.101*
O30.2566 (4)−0.2053 (4)0.7859 (4)0.215 (3)
N50.2985 (4)−0.1807 (3)0.9457 (5)0.1136 (19)
C210.3201 (5)−0.2117 (4)0.8616 (5)0.113 (2)
H21A0.3899−0.24030.86220.135*
C220.1947 (7)−0.1350 (6)0.9424 (6)0.187 (4)
H22A0.1688−0.11420.87780.281*
H22B0.2072−0.08710.98640.281*
H22C0.1370−0.17250.96080.281*
C230.3818 (6)−0.1888 (5)1.0310 (5)0.157 (3)
H23A0.4456−0.22291.01770.236*
H23B0.3472−0.21651.08030.236*
H23C0.4090−0.13271.05290.236*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0350 (3)0.0512 (3)0.0443 (3)0.0053 (3)0.0072 (2)−0.0028 (3)
Cl10.0529 (5)0.0601 (6)0.0785 (7)−0.0063 (5)0.0268 (5)−0.0082 (5)
O10.0447 (14)0.0578 (17)0.0600 (17)0.0097 (13)0.0026 (13)0.0087 (13)
O1W0.0550 (16)0.0710 (19)0.075 (2)−0.0168 (14)−0.0118 (14)0.0187 (16)
O20.0782 (19)0.115 (3)0.0513 (19)0.0413 (18)−0.0050 (15)−0.0195 (17)
N10.0363 (15)0.0497 (18)0.0422 (17)−0.0003 (14)0.0071 (13)−0.0009 (14)
N20.0398 (16)0.0475 (18)0.0481 (18)−0.0007 (14)0.0066 (14)−0.0016 (14)
N30.0397 (16)0.0483 (19)0.0474 (19)0.0026 (14)0.0060 (14)−0.0056 (14)
N40.0363 (15)0.0553 (19)0.0471 (18)0.0079 (14)0.0064 (14)−0.0022 (15)
C10.0381 (18)0.040 (2)0.053 (2)−0.0005 (16)0.0104 (17)−0.0022 (17)
C20.0423 (19)0.041 (2)0.058 (2)0.0059 (17)0.0147 (18)−0.0037 (18)
C30.063 (2)0.063 (3)0.060 (3)0.011 (2)0.010 (2)−0.009 (2)
C40.070 (3)0.067 (3)0.074 (3)0.018 (2)0.015 (2)−0.021 (2)
C50.055 (2)0.053 (3)0.095 (3)0.014 (2)0.020 (2)−0.009 (2)
C60.042 (2)0.049 (2)0.070 (3)0.0067 (18)0.0124 (19)0.003 (2)
C70.0376 (19)0.037 (2)0.058 (2)−0.0066 (16)0.0102 (18)0.0058 (18)
C80.0390 (19)0.041 (2)0.050 (2)−0.0031 (16)0.0071 (17)0.0077 (17)
C90.053 (2)0.055 (3)0.052 (2)−0.0071 (19)0.0039 (19)0.010 (2)
C100.065 (3)0.057 (2)0.047 (2)−0.019 (2)0.007 (2)0.000 (2)
C110.071 (3)0.070 (3)0.056 (3)−0.009 (2)0.019 (2)−0.009 (2)
C120.054 (2)0.065 (3)0.058 (3)0.007 (2)0.013 (2)−0.007 (2)
C130.046 (2)0.063 (3)0.045 (2)0.007 (2)0.0024 (18)−0.008 (2)
C140.0376 (18)0.046 (2)0.052 (2)0.0015 (17)0.0057 (17)−0.0040 (18)
C150.045 (2)0.055 (2)0.048 (2)−0.0004 (19)0.0014 (18)−0.0031 (19)
C160.0375 (19)0.047 (2)0.068 (3)0.0014 (18)0.0089 (18)0.006 (2)
C170.048 (2)0.060 (3)0.070 (3)0.011 (2)0.015 (2)−0.007 (2)
C180.051 (2)0.066 (3)0.055 (2)0.008 (2)0.0115 (19)−0.009 (2)
C190.105 (4)0.090 (3)0.049 (3)−0.020 (3)0.010 (3)−0.001 (2)
C200.056 (2)0.069 (3)0.076 (3)0.013 (2)0.008 (2)0.008 (2)
O30.173 (4)0.262 (6)0.166 (4)−0.105 (4)−0.094 (3)0.137 (4)
N50.078 (3)0.081 (3)0.176 (6)0.003 (3)0.006 (3)−0.001 (3)
C210.080 (4)0.098 (4)0.154 (6)−0.018 (3)0.004 (4)0.052 (4)
C220.166 (7)0.259 (11)0.134−0.005 (8)0.017 (6)−0.035 (7)
C230.176 (7)0.166 (7)0.111 (6)−0.031 (6)−0.026 (5)0.007 (5)
Geometric parameters (Å, °) top
Mn1—N41.923 (3)C10—C111.382 (6)
Mn1—N11.941 (3)C10—C191.495 (5)
Mn1—N22.066 (3)C11—C121.380 (5)
Mn1—N32.071 (3)C11—H11A0.9300
Mn1—O1W2.273 (3)C12—H12A0.9300
Mn1—Cl12.4628 (12)C13—C141.506 (5)
O1—C71.237 (4)C14—C151.382 (5)
O1W—H1WA0.8582C15—C161.386 (5)
O1W—H1WB0.8600C15—H15A0.9300
O2—C131.223 (5)C16—C171.373 (6)
N1—C71.351 (4)C16—C201.519 (5)
N1—C11.413 (4)C17—C181.389 (5)
N2—C121.343 (5)C17—H17A0.9300
N2—C81.350 (4)C18—H18A0.9300
N3—C181.324 (5)C19—H19A0.9600
N3—C141.337 (5)C19—H19B0.9600
N4—C131.358 (4)C19—H19C0.9600
N4—C21.405 (4)C20—H20A0.9600
C1—C61.396 (5)C20—H20B0.9600
C1—C21.405 (5)C20—H20C0.9600
C2—C31.380 (5)O3—C211.190 (7)
C3—C41.376 (5)N5—C211.336 (8)
C3—H3A0.9300N5—C221.401 (9)
C4—C51.356 (6)N5—C231.413 (7)
C4—H4A0.9300C21—H21A0.9300
C5—C61.384 (6)C22—H22A0.9600
C5—H5A0.9300C22—H22B0.9600
C6—H6A0.9300C22—H22C0.9600
C7—C81.492 (5)C23—H23A0.9600
C8—C91.371 (5)C23—H23B0.9600
C9—C101.386 (6)C23—H23C0.9600
C9—H9A0.9300
N4—Mn1—N181.29 (12)C11—C10—C9117.1 (4)
N4—Mn1—N2161.16 (12)C11—C10—C19121.9 (4)
N1—Mn1—N280.28 (12)C9—C10—C19121.0 (4)
N4—Mn1—N380.40 (12)C12—C11—C10119.8 (4)
N1—Mn1—N3160.75 (12)C12—C11—H11A120.1
N2—Mn1—N3117.43 (12)C10—C11—H11A120.1
N4—Mn1—O1W98.45 (12)N2—C12—C11122.8 (4)
N1—Mn1—O1W96.71 (11)N2—C12—H12A118.6
N2—Mn1—O1W79.93 (11)C11—C12—H12A118.6
N3—Mn1—O1W80.21 (10)O2—C13—N4127.2 (4)
N4—Mn1—Cl198.18 (9)O2—C13—C14121.3 (3)
N1—Mn1—Cl199.69 (9)N4—C13—C14111.5 (3)
N2—Mn1—Cl188.73 (9)N3—C14—C15122.5 (3)
N3—Mn1—Cl188.75 (9)N3—C14—C13115.6 (3)
O1W—Mn1—Cl1158.17 (9)C15—C14—C13121.9 (3)
Mn1—O1W—H1WA126.9C14—C15—C16119.5 (4)
Mn1—O1W—H1WB118.6C14—C15—H15A120.3
H1WA—O1W—H1WB106.6C16—C15—H15A120.3
C7—N1—C1125.5 (3)C17—C16—C15117.2 (3)
C7—N1—Mn1118.9 (2)C17—C16—C20122.0 (4)
C1—N1—Mn1115.6 (2)C15—C16—C20120.8 (4)
C12—N2—C8117.6 (3)C16—C17—C18120.5 (4)
C12—N2—Mn1129.4 (3)C16—C17—H17A119.7
C8—N2—Mn1113.0 (2)C18—C17—H17A119.7
C18—N3—C14118.5 (3)N3—C18—C17121.8 (4)
C18—N3—Mn1128.5 (3)N3—C18—H18A119.1
C14—N3—Mn1113.0 (2)C17—C18—H18A119.1
C13—N4—C2124.3 (3)C10—C19—H19A109.5
C13—N4—Mn1119.5 (2)C10—C19—H19B109.5
C2—N4—Mn1116.2 (2)H19A—C19—H19B109.5
C6—C1—C2119.9 (3)C10—C19—H19C109.5
C6—C1—N1127.0 (3)H19A—C19—H19C109.5
C2—C1—N1113.0 (3)H19B—C19—H19C109.5
C3—C2—C1119.5 (3)C16—C20—H20A109.5
C3—C2—N4127.0 (3)C16—C20—H20B109.5
C1—C2—N4113.5 (3)H20A—C20—H20B109.5
C4—C3—C2119.6 (4)C16—C20—H20C109.5
C4—C3—H3A120.2H20A—C20—H20C109.5
C2—C3—H3A120.2H20B—C20—H20C109.5
C5—C4—C3121.2 (4)C21—N5—C22116.6 (6)
C5—C4—H4A119.4C21—N5—C23120.4 (6)
C3—C4—H4A119.4C22—N5—C23122.8 (7)
C4—C5—C6120.9 (4)O3—C21—N5124.9 (7)
C4—C5—H5A119.5O3—C21—H21A117.5
C6—C5—H5A119.5N5—C21—H21A117.5
C5—C6—C1118.7 (4)N5—C22—H22A109.5
C5—C6—H6A120.6N5—C22—H22B109.5
C1—C6—H6A120.6H22A—C22—H22B109.5
O1—C7—N1126.6 (3)N5—C22—H22C109.5
O1—C7—C8121.0 (3)H22A—C22—H22C109.5
N1—C7—C8112.4 (3)H22B—C22—H22C109.5
N2—C8—C9122.0 (3)N5—C23—H23A109.5
N2—C8—C7115.3 (3)N5—C23—H23B109.5
C9—C8—C7122.6 (3)H23A—C23—H23B109.5
C8—C9—C10120.7 (4)N5—C23—H23C109.5
C8—C9—H9A119.7H23A—C23—H23C109.5
C10—C9—H9A119.7H23B—C23—H23C109.5
N4—Mn1—N1—C7−177.1 (3)C1—C2—C3—C42.6 (6)
N2—Mn1—N1—C7−1.0 (2)N4—C2—C3—C4−179.9 (4)
N3—Mn1—N1—C7−159.0 (3)C2—C3—C4—C5−1.2 (7)
O1W—Mn1—N1—C7−79.5 (3)C3—C4—C5—C6−0.1 (7)
Cl1—Mn1—N1—C786.0 (2)C4—C5—C6—C1−0.2 (6)
N4—Mn1—N1—C15.2 (2)C2—C1—C6—C51.6 (5)
N2—Mn1—N1—C1−178.7 (3)N1—C1—C6—C5−176.8 (4)
N3—Mn1—N1—C123.3 (5)C1—N1—C7—O1−2.1 (6)
O1W—Mn1—N1—C1102.7 (2)Mn1—N1—C7—O1−179.6 (3)
Cl1—Mn1—N1—C1−91.7 (2)C1—N1—C7—C8177.7 (3)
N4—Mn1—N2—C12−167.7 (4)Mn1—N1—C7—C80.2 (4)
N1—Mn1—N2—C12−179.7 (3)C12—N2—C8—C90.0 (5)
N3—Mn1—N2—C12−7.7 (4)Mn1—N2—C8—C9178.8 (3)
O1W—Mn1—N2—C12−81.0 (3)C12—N2—C8—C7179.2 (3)
Cl1—Mn1—N2—C1280.2 (3)Mn1—N2—C8—C7−2.0 (4)
N4—Mn1—N2—C813.6 (5)O1—C7—C8—N2−179.0 (3)
N1—Mn1—N2—C81.6 (2)N1—C7—C8—N21.2 (4)
N3—Mn1—N2—C8173.7 (2)O1—C7—C8—C90.2 (5)
O1W—Mn1—N2—C8100.3 (2)N1—C7—C8—C9−179.5 (3)
Cl1—Mn1—N2—C8−98.4 (2)N2—C8—C9—C10−0.8 (5)
N4—Mn1—N3—C18178.9 (3)C7—C8—C9—C10−179.9 (3)
N1—Mn1—N3—C18160.8 (3)C8—C9—C10—C111.4 (6)
N2—Mn1—N3—C185.3 (4)C8—C9—C10—C19−179.7 (4)
O1W—Mn1—N3—C1878.5 (3)C9—C10—C11—C12−1.2 (6)
Cl1—Mn1—N3—C18−82.6 (3)C19—C10—C11—C12179.9 (4)
N4—Mn1—N3—C14−1.4 (2)C8—N2—C12—C110.2 (6)
N1—Mn1—N3—C14−19.6 (5)Mn1—N2—C12—C11−178.4 (3)
N2—Mn1—N3—C14−175.0 (2)C10—C11—C12—N20.4 (6)
O1W—Mn1—N3—C14−101.8 (3)C2—N4—C13—O22.3 (7)
Cl1—Mn1—N3—C1497.1 (2)Mn1—N4—C13—O2−179.1 (4)
N1—Mn1—N4—C13175.0 (3)C2—N4—C13—C14−178.9 (3)
N2—Mn1—N4—C13163.0 (3)Mn1—N4—C13—C14−0.3 (4)
N3—Mn1—N4—C130.9 (3)C18—N3—C14—C150.4 (5)
O1W—Mn1—N4—C1379.4 (3)Mn1—N3—C14—C15−179.3 (3)
Cl1—Mn1—N4—C13−86.4 (3)C18—N3—C14—C13−178.6 (3)
N1—Mn1—N4—C2−6.4 (2)Mn1—N3—C14—C131.7 (4)
N2—Mn1—N4—C2−18.3 (5)O2—C13—C14—N3177.9 (4)
N3—Mn1—N4—C2179.6 (3)N4—C13—C14—N3−1.0 (5)
O1W—Mn1—N4—C2−101.9 (3)O2—C13—C14—C15−1.0 (6)
Cl1—Mn1—N4—C292.3 (2)N4—C13—C14—C15−180.0 (3)
C7—N1—C1—C6−2.1 (6)N3—C14—C15—C16−0.4 (6)
Mn1—N1—C1—C6175.4 (3)C13—C14—C15—C16178.6 (3)
C7—N1—C1—C2179.3 (3)C14—C15—C16—C17−0.1 (5)
Mn1—N1—C1—C2−3.1 (4)C14—C15—C16—C20−179.2 (3)
C6—C1—C2—C3−2.9 (5)C15—C16—C17—C180.6 (6)
N1—C1—C2—C3175.8 (3)C20—C16—C17—C18179.6 (4)
C6—C1—C2—N4179.3 (3)C14—N3—C18—C170.1 (6)
N1—C1—C2—N4−2.0 (4)Mn1—N3—C18—C17179.8 (3)
C13—N4—C2—C37.4 (6)C16—C17—C18—N3−0.6 (6)
Mn1—N4—C2—C3−171.2 (3)C22—N5—C21—O3−2.2 (10)
C13—N4—C2—C1−175.0 (3)C23—N5—C21—O3−177.5 (6)
Mn1—N4—C2—C16.4 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O1i0.861.902.728 (3)162.3
O1W—H1WB···O3i0.861.782.627 (5)170.2
Symmetry codes: (i) −x, −y, −z+1; i.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O1i0.861.902.728 (3)162.3
O1W—H1WB···O3i0.861.782.627 (5)170.2
Symmetry codes: (i) −x, −y, −z+1; i.
Acknowledgements top

This project was sponsored by the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry of China. We also thank the State Key Laboratory of Coordination Chemistry of Nanjing University and Sichuan University for financial support.

references
References top

Bruker (1997). SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Hureau, C., Blondin, G., Charlot, M. F., Philouze, C., Nierlich, M., Cesario, M. & Anxolabehere-Mallart, E. (2005). Inorg. Chem. 44, 3669–3683.

Larson, E. J. & Pecoraro, V. L. (1992). In Manganese Redox Enzymes, edited by V. L. Pecoraro, pp. 1–28. New York: VCH Publishers.

Liang, L., Qu, Y.-Y., Yang, L. & Zhou, X.-G. (2007). Acta Cryst. E63, m1503–m1505.

Ray, M., Mukherjee, S., Richardson, J. F. & Buchanan, R. M. (1993). J. Chem. Soc. Dalton Trans. pp. 2451–2457.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXS97 and SHELXS97. University of Göttingen, Germany.