PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m124–m125.
Published online 2007 December 6. doi:  10.1107/S1600536807064240
PMCID: PMC2915075

Chlorido{4,4′-dichloro-2,2′-[1,2-phenyl­enebis(nitrilo­methyl­idyne)]diphenolato-κ4 O,N,N′,O′}(methanol-κO)manganese(III)

Abstract

In the title complex, [Mn(C20H12Cl2N2O2)Cl(CH3OH)], the MnIII atom is in an octa­hedral coordination geometry with the N2O2 atoms of the doubly-deprotonated Schiff base forming a square around it. The chloride ion and the O atom of the methanol mol­ecule occupy the other two positions of the octa­hedron. The dihedral angle between the two outer phenolate rings of the tetra­dentate ligand is 20.27 (12)°. The central phenyl­ene ring makes dihedral angles of 18.62 (12) and 6.02 (12)° with the two outer phenolate rings. Hydrogen bonds of the O—H(...)Cl type link the mol­ecules into an infinite chain along [010]. These chains are arranged into sheets parallel to the ab plane and these sheets are connected by weak C—H(...)Cl inter­actions into a three-dimensional network. The crystal structure is further stabilized by C—H(...)π inter­actions.

Related literature

For related structures see, for examples: Eltayeb et al. (2007 [triangle]); Habibi et al. (2007 [triangle]); Mitra et al. (2006 [triangle]); Naskar et al. (2004 [triangle]). For related literature on applications of manganese complexes, see for example: Dixit & Srinivasan (1988 [triangle]); Glatzel et al. (2004 [triangle]); Lu et al. (2006 [triangle]); Stallings et al. (1985 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m124-scheme1.jpg

Experimental

Crystal data

  • [Mn(C20H12Cl2N2O2)Cl(CH4O)]
  • M r = 505.65
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m124-efi1.jpg
  • a = 15.9183 (4) Å
  • b = 6.6305 (2) Å
  • c = 23.3399 (6) Å
  • β = 124.672 (2)°
  • V = 2025.99 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.07 mm−1
  • T = 100.0 (1) K
  • 0.56 × 0.09 × 0.04 mm

Data collection

  • Bruker SMART APEX2 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.584, T max = 0.963
  • 22773 measured reflections
  • 5384 independent reflections
  • 4153 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.108
  • S = 1.09
  • 5384 reflections
  • 272 parameters
  • H-atom parameters constrained
  • Δρmax = 1.55 e Å−3
  • Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXTL (Sheldrick, 1998 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064240/ng2401sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064240/ng2401Isup2.hkl

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

Acknowledgments

The authors thank the Malaysian Government, Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia for the E-Science Fund research grant (PKIMIA/613308) and facilities. The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. The authors also thank Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS) grant No. 203/PFIZIK/671064.

supplementary crystallographic information

Comment

The coordination chemistry of manganese complexes in various oxidation states and in various combinations of nitrogen and oxygen donor environment has been extensively investigated, espectially manganese complexes with Schiff base ligands which have attracted considerable interest in the past decades and recently, due to their importance and variety of applications in chemistry, biology, physics and advanced materials. They have been used as models for oxygen-evolving complex of photosystem II (Glatzel et al., 2004), catalysis (Dixit & Srinivasan, 1988), single-molecule magnet (Lu et al., 2006) and as active sites of manganese-containing metal enzymes (Stallings et al., 1985). Recently, we reported the crystal structure MnIII with Schiff base ligand (Eltayeb et al., 2007) and herein the crystal structure of the MnIII complex with 2,2'-{1,2-phenylenebis(nitrilomethylidyne)}bis(4-chlorophenol) is reported.

In the title complex molecule (Fig. 1), MnIII coordinates with the dianionic tetradentate Schiff base ligand through two imine N atoms and two phenolato O atoms in the basal plane (N1, N2, O1 and O2) and the chloride ion and methanol molecule in the axial positions. The in-plane Mn—O distances [Mn1—O1 = 1.8834 (15) Å and Mn1—O2 = 1.8668 (16) Å] and Mn—N distances [Mn1—N1 = 1.9860 (19) Å and Mn1—N2 = 2.0005 (18) Å are quite similar to that observed in other six coordination MnIII complexes of Schiff base ligands (Eltayeb et al., 2007; Habibi et al., 2007; Mitra et al., 2006; Naskar et al., 2004). The two axially ligated chloride ion and methanol molecule experience the usual Jahn Teller distortion of the MnIII oxidation state, which was indicated by the Mn1—O5 = 2.3247 (19) Å and Mn1—Cl1 = 2.5493 (7) Å bond elongation as have been found previously (Eltayeb et al., 2007; Habibi et al., 2007). The dihedral angle between the two outer phenolate rings [(C1–C6) and C15–C20) of the tetradentate ligand is 20.27 (12) °. The central benzene ring (C8–C13) makes the dihedral angles of 18.62(12 ° and 6.02 (12) ° with the two outer phenolate rings respectively. Bond lengths and angles in the Schiff base ligand are very similar to those reported for the other MnIII complexes with similar ligands (Eltayeb et al., 2007; Habibi et al., 2007; Mitra et al., 2006; Naskar et al., 2004).

In the crystal packing (Fig. 2), O—H···Cl hydrogen bonds [O3—H1O3···Cl1; symmetry code x, 1 + y, z (Table 1)] link the molecules into infinite chains along the [0 1 0] direction. These chains are arranged into sheets parallel to the ab plane and these sheets are connect by weak C—H···Cl interactons (Table 1). The crystal is further stabilized by C—H···π interactions (Table 1); Cg1, Cg2 and Cg3 are the centroids of C1–C6, C8–C13 and C15–C20 benzene rings, respectively.

Experimental

The title compound was synthesized by adding 5-chloro-2-hydroxybenzaldehyde (0.626 g, 4 mmol) into a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol 95% (30 ml). The mixture was refluxed with stirring for half an hour. Manganese chloride tetrahydrate (0.394 g, 2 mmol) in ethanol (10 ml) was then added, followed by triethylamine (0.5 ml, 3.6 mmol). The mixture was refluxed at room temperature for three hours. A brown precipitate was obtained, washed by about 5 ml e thanol, dried, and then washed with copious quantities of diethyl ether. Brown single crystals of the title compound suitable for x-ray structure determination were recrystallized from methanol by slow evaporation of the solvent at room temperature over several days.

Refinement

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances in the ranges 0.93–0.96 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is located at 0.68 Å from H21A and the deepest hole is located at 0.35 Å from C21.

Figures

Fig. 1.
The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering.
Fig. 2.
The crystal packing of (I), viewed along the c axis showing the chains running along [0 1 0] direction. Hydrogen bonds are drawn as dash lines.

Crystal data

[Mn(C20H12N2O2Cl2)Cl(CH4O)]F000 = 1024
Mr = 505.65Dx = 1.658 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5384 reflections
a = 15.9183 (4) Åθ = 1.5–29.0º
b = 6.6305 (2) ŵ = 1.07 mm1
c = 23.3399 (6) ÅT = 100.0 (1) K
β = 124.672 (2)ºNeedle, brown
V = 2025.99 (10) Å30.56 × 0.09 × 0.04 mm
Z = 4

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer5384 independent reflections
Radiation source: medium-focus sealed tube4153 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.054
Detector resolution: 8.33 pixels mm-1θmax = 29.0º
T = 100.0(1) Kθmin = 1.6º
ω scansh = −21→21
Absorption correction: multi-scan(SADABS; Bruker, 2005)k = −9→9
Tmin = 0.584, Tmax = 0.963l = −31→31
22773 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)] = 0.042H-atom parameters constrained
wR(F2) = 0.108  w = 1/[σ2(Fo2) + (0.047P)2 + 0.9163P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.002
5384 reflectionsΔρmax = 1.55 e Å3
272 parametersΔρmin = −0.47 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
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)

xyzUiso*/Ueq
Mn10.38124 (2)0.58871 (6)0.592785 (16)0.01538 (10)
Cl10.34939 (4)0.25637 (10)0.52850 (3)0.01860 (13)
Cl2−0.09275 (5)0.72592 (12)0.56471 (3)0.02870 (16)
Cl30.92504 (4)0.60705 (12)0.74512 (3)0.02954 (17)
O10.31347 (12)0.5137 (3)0.63441 (8)0.0189 (4)
O20.50867 (12)0.5203 (3)0.67240 (8)0.0189 (4)
O30.39833 (13)0.9150 (3)0.63460 (8)0.0220 (4)
H1O30.37590.98890.60410.026*
N10.25509 (14)0.7054 (3)0.51017 (9)0.0158 (4)
N20.44238 (14)0.6915 (3)0.54358 (9)0.0150 (4)
C10.22094 (17)0.5628 (4)0.61572 (12)0.0184 (5)
C20.18875 (18)0.4945 (4)0.65745 (12)0.0220 (5)
H2A0.23250.41550.69630.026*
C30.09306 (19)0.5431 (4)0.64153 (12)0.0231 (6)
H3A0.07280.49520.66940.028*
C40.02714 (17)0.6633 (4)0.58403 (12)0.0214 (5)
C50.05423 (18)0.7289 (4)0.54092 (12)0.0210 (5)
H5A0.00880.80590.50190.025*
C60.15150 (17)0.6792 (4)0.55588 (12)0.0183 (5)
C70.17185 (17)0.7418 (4)0.50609 (11)0.0183 (5)
H7A0.12110.81460.46770.022*
C80.26702 (17)0.7624 (4)0.45641 (11)0.0152 (5)
C90.18680 (17)0.8169 (4)0.38927 (11)0.0189 (5)
H9A0.12000.81630.37690.023*
C100.20691 (18)0.8716 (4)0.34132 (11)0.0198 (5)
H10A0.15350.90840.29650.024*
C110.30626 (18)0.8721 (4)0.35933 (12)0.0198 (5)
H11A0.31890.91020.32650.024*
C120.38699 (17)0.8165 (4)0.42562 (11)0.0173 (5)
H12A0.45350.81740.43750.021*
C130.36721 (16)0.7592 (4)0.47441 (11)0.0148 (4)
C140.53947 (17)0.6908 (4)0.56893 (11)0.0163 (5)
H14A0.55870.73690.54030.020*
C150.61905 (16)0.6240 (4)0.63775 (11)0.0159 (5)
C160.72077 (17)0.6399 (4)0.65662 (12)0.0189 (5)
H16A0.73330.68810.62470.023*
C170.80005 (17)0.5842 (4)0.72182 (12)0.0211 (5)
C180.78387 (18)0.5105 (4)0.77090 (12)0.0227 (5)
H18A0.83910.47580.81540.027*
C190.68541 (18)0.4893 (4)0.75304 (11)0.0210 (5)
H19A0.67480.43760.78550.025*
C200.60042 (17)0.5451 (4)0.68617 (11)0.0165 (5)
C210.4985 (2)0.9955 (5)0.69176 (13)0.0304 (6)
H21A0.49011.13030.70270.046*
H21B0.54440.99680.67750.046*
H21C0.52610.91160.73220.046*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn10.01368 (16)0.0184 (2)0.01457 (16)0.00078 (15)0.00836 (13)0.00217 (15)
Cl10.0184 (3)0.0183 (3)0.0200 (2)−0.0003 (2)0.0115 (2)0.0002 (2)
Cl20.0230 (3)0.0326 (4)0.0394 (3)−0.0020 (3)0.0231 (3)−0.0054 (3)
Cl30.0130 (3)0.0404 (4)0.0285 (3)0.0003 (3)0.0078 (2)−0.0028 (3)
O10.0176 (7)0.0222 (10)0.0184 (7)0.0017 (8)0.0112 (6)0.0044 (7)
O20.0162 (7)0.0230 (10)0.0164 (7)0.0010 (8)0.0087 (6)0.0033 (7)
O30.0265 (9)0.0200 (10)0.0194 (7)0.0006 (8)0.0130 (7)0.0015 (7)
N10.0153 (8)0.0171 (11)0.0151 (8)0.0004 (8)0.0086 (7)0.0011 (8)
N20.0145 (8)0.0158 (11)0.0153 (8)0.0012 (8)0.0088 (7)0.0006 (8)
C10.0179 (10)0.0187 (14)0.0201 (10)−0.0025 (10)0.0116 (9)−0.0034 (10)
C20.0247 (12)0.0209 (14)0.0224 (11)−0.0028 (11)0.0146 (10)−0.0015 (11)
C30.0263 (12)0.0258 (15)0.0248 (11)−0.0079 (12)0.0191 (10)−0.0060 (11)
C40.0175 (11)0.0230 (14)0.0273 (11)−0.0049 (11)0.0149 (10)−0.0085 (11)
C50.0172 (10)0.0220 (14)0.0246 (11)−0.0017 (11)0.0124 (9)−0.0024 (11)
C60.0168 (10)0.0193 (13)0.0202 (10)−0.0011 (10)0.0114 (9)−0.0005 (10)
C70.0158 (10)0.0214 (14)0.0165 (9)0.0013 (10)0.0085 (8)0.0019 (10)
C80.0173 (10)0.0143 (12)0.0162 (9)−0.0007 (10)0.0110 (8)−0.0002 (9)
C90.0133 (10)0.0237 (14)0.0158 (10)0.0010 (10)0.0061 (8)0.0005 (10)
C100.0195 (11)0.0204 (14)0.0153 (10)0.0007 (11)0.0073 (9)0.0031 (10)
C110.0251 (12)0.0180 (13)0.0185 (10)0.0021 (11)0.0136 (9)0.0018 (10)
C120.0161 (10)0.0180 (13)0.0182 (10)−0.0008 (10)0.0100 (9)−0.0023 (10)
C130.0170 (10)0.0118 (12)0.0148 (9)0.0001 (10)0.0085 (8)−0.0014 (9)
C140.0189 (10)0.0145 (13)0.0166 (9)−0.0002 (10)0.0108 (9)−0.0014 (9)
C150.0158 (10)0.0128 (12)0.0182 (10)0.0019 (10)0.0092 (9)0.0002 (9)
C160.0181 (11)0.0165 (13)0.0214 (10)0.0002 (10)0.0109 (9)−0.0022 (10)
C170.0141 (10)0.0203 (14)0.0244 (11)0.0008 (10)0.0082 (9)−0.0028 (11)
C180.0173 (11)0.0222 (15)0.0189 (10)0.0042 (11)0.0044 (9)0.0007 (11)
C190.0214 (11)0.0218 (14)0.0174 (10)0.0008 (11)0.0096 (9)0.0017 (10)
C200.0166 (10)0.0127 (12)0.0174 (10)0.0015 (10)0.0079 (8)−0.0009 (9)
C210.0342 (14)0.0317 (17)0.0294 (13)−0.0008 (14)0.0206 (12)−0.0032 (13)

Geometric parameters (Å, °)

Mn1—O21.8668 (16)C7—H7A0.9300
Mn1—O11.8834 (15)C8—C91.393 (3)
Mn1—N11.9860 (19)C8—C131.399 (3)
Mn1—N22.0005 (18)C9—C101.376 (3)
Mn1—O32.3247 (19)C9—H9A0.9300
Mn1—Cl12.5493 (7)C10—C111.386 (3)
Cl2—C41.743 (2)C10—H10A0.9301
Cl3—C171.745 (2)C11—C121.385 (3)
O1—C11.317 (3)C11—H11A0.9299
O2—C201.315 (3)C12—C131.396 (3)
O3—C211.479 (3)C12—H12A0.9300
O3—H1O30.7642C14—C151.437 (3)
N1—C71.296 (3)C14—H14A0.9302
N1—C81.423 (3)C15—C161.420 (3)
N2—C141.303 (3)C15—C201.421 (3)
N2—C131.429 (3)C16—C171.364 (3)
C1—C21.408 (3)C16—H16A0.9300
C1—C61.419 (3)C17—C181.398 (3)
C2—C31.385 (3)C18—C191.381 (3)
C2—H2A0.9298C18—H18A0.9300
C3—C41.391 (4)C19—C201.414 (3)
C3—H3A0.9300C19—H19A0.9298
C4—C51.372 (3)C21—H21A0.9600
C5—C61.419 (3)C21—H21B0.9600
C5—H5A0.9300C21—H21C0.9600
C6—C71.434 (3)
O2—Mn1—O192.25 (7)C6—C7—H7A117.3
O2—Mn1—N1170.80 (9)C9—C8—C13120.02 (19)
O1—Mn1—N192.54 (7)C9—C8—N1124.35 (19)
O2—Mn1—N292.65 (7)C13—C8—N1115.63 (19)
O1—Mn1—N2173.99 (8)C10—C9—C8119.7 (2)
N1—Mn1—N282.14 (8)C10—C9—H9A120.2
O2—Mn1—O390.40 (7)C8—C9—H9A120.2
O1—Mn1—O389.64 (7)C9—C10—C11120.5 (2)
N1—Mn1—O381.79 (8)C9—C10—H10A119.8
N2—Mn1—O386.84 (7)C11—C10—H10A119.8
O2—Mn1—Cl196.63 (6)C12—C11—C10120.8 (2)
O1—Mn1—Cl195.44 (6)C12—C11—H11A119.6
N1—Mn1—Cl190.72 (6)C10—C11—H11A119.6
N2—Mn1—Cl187.45 (6)C11—C12—C13119.2 (2)
O3—Mn1—Cl1171.14 (4)C11—C12—H12A120.4
C1—O1—Mn1128.67 (15)C13—C12—H12A120.4
C20—O2—Mn1129.77 (14)C12—C13—C8119.9 (2)
C21—O3—Mn1121.53 (16)C12—C13—N2125.09 (19)
C21—O3—H1O3107.5C8—C13—N2115.00 (18)
Mn1—O3—H1O3109.0N2—C14—C15124.9 (2)
C7—N1—C8121.98 (19)N2—C14—H14A117.5
C7—N1—Mn1124.80 (15)C15—C14—H14A117.6
C8—N1—Mn1113.03 (14)C16—C15—C20119.9 (2)
C14—N2—C13121.91 (18)C16—C15—C14116.6 (2)
C14—N2—Mn1125.22 (15)C20—C15—C14123.5 (2)
C13—N2—Mn1112.80 (13)C17—C16—C15119.6 (2)
O1—C1—C2118.0 (2)C17—C16—H16A120.2
O1—C1—C6124.0 (2)C15—C16—H16A120.2
C2—C1—C6118.0 (2)C16—C17—C18121.6 (2)
C3—C2—C1121.1 (2)C16—C17—Cl3119.44 (19)
C3—C2—H2A119.4C18—C17—Cl3118.94 (18)
C1—C2—H2A119.4C19—C18—C17119.7 (2)
C2—C3—C4120.2 (2)C19—C18—H18A120.2
C2—C3—H3A119.9C17—C18—H18A120.2
C4—C3—H3A119.9C18—C19—C20121.0 (2)
C5—C4—C3120.7 (2)C18—C19—H19A119.5
C5—C4—Cl2119.3 (2)C20—C19—H19A119.5
C3—C4—Cl2120.00 (18)O2—C20—C19118.0 (2)
C4—C5—C6120.0 (2)O2—C20—C15123.8 (2)
C4—C5—H5A120.0C19—C20—C15118.2 (2)
C6—C5—H5A120.0O3—C21—H21A109.5
C5—C6—C1119.9 (2)O3—C21—H21B109.5
C5—C6—C7116.8 (2)H21A—C21—H21B109.5
C1—C6—C7123.1 (2)O3—C21—H21C109.5
N1—C7—C6125.4 (2)H21A—C21—H21C109.5
N1—C7—H7A117.3H21B—C21—H21C109.5
O2—Mn1—O1—C1162.1 (2)C8—N1—C7—C6176.2 (2)
N1—Mn1—O1—C1−10.1 (2)Mn1—N1—C7—C6−9.2 (4)
O3—Mn1—O1—C171.7 (2)C5—C6—C7—N1−178.1 (2)
Cl1—Mn1—O1—C1−101.0 (2)C1—C6—C7—N1−1.8 (4)
O1—Mn1—O2—C20−174.3 (2)C7—N1—C8—C9−15.6 (4)
N2—Mn1—O2—C202.2 (2)Mn1—N1—C8—C9169.1 (2)
O3—Mn1—O2—C20−84.6 (2)C7—N1—C8—C13165.0 (2)
Cl1—Mn1—O2—C2089.9 (2)Mn1—N1—C8—C13−10.2 (3)
O2—Mn1—O3—C2116.48 (16)C13—C8—C9—C10−1.4 (4)
O1—Mn1—O3—C21108.72 (16)N1—C8—C9—C10179.3 (2)
N1—Mn1—O3—C21−158.66 (16)C8—C9—C10—C110.2 (4)
N2—Mn1—O3—C21−76.15 (16)C9—C10—C11—C120.4 (4)
O1—Mn1—N1—C712.8 (2)C10—C11—C12—C130.1 (4)
N2—Mn1—N1—C7−164.4 (2)C11—C12—C13—C8−1.3 (4)
O3—Mn1—N1—C7−76.5 (2)C11—C12—C13—N2177.6 (2)
Cl1—Mn1—N1—C7108.3 (2)C9—C8—C13—C121.9 (4)
O1—Mn1—N1—C8−172.10 (17)N1—C8—C13—C12−178.7 (2)
N2—Mn1—N1—C810.70 (17)C9—C8—C13—N2−177.1 (2)
O3—Mn1—N1—C898.63 (17)N1—C8—C13—N22.3 (3)
Cl1—Mn1—N1—C8−76.62 (16)C14—N2—C13—C124.8 (4)
O2—Mn1—N2—C141.1 (2)Mn1—N2—C13—C12−172.3 (2)
N1—Mn1—N2—C14173.5 (2)C14—N2—C13—C8−176.3 (2)
O3—Mn1—N2—C1491.4 (2)Mn1—N2—C13—C86.6 (3)
Cl1—Mn1—N2—C14−95.4 (2)C13—N2—C14—C15−179.7 (2)
O2—Mn1—N2—C13178.13 (16)Mn1—N2—C14—C15−2.9 (4)
N1—Mn1—N2—C13−9.49 (16)N2—C14—C15—C16−178.3 (2)
O3—Mn1—N2—C13−91.62 (16)N2—C14—C15—C201.7 (4)
Cl1—Mn1—N2—C1381.60 (16)C20—C15—C16—C17−1.8 (4)
Mn1—O1—C1—C2−177.18 (18)C14—C15—C16—C17178.3 (2)
Mn1—O1—C1—C63.2 (4)C15—C16—C17—C180.3 (4)
O1—C1—C2—C3179.0 (2)C15—C16—C17—Cl3−179.2 (2)
C6—C1—C2—C3−1.4 (4)C16—C17—C18—C191.2 (4)
C1—C2—C3—C4−0.8 (4)Cl3—C17—C18—C19−179.3 (2)
C2—C3—C4—C52.5 (4)C17—C18—C19—C20−1.3 (4)
C2—C3—C4—Cl2−179.4 (2)Mn1—O2—C20—C19176.37 (18)
C3—C4—C5—C6−1.9 (4)Mn1—O2—C20—C15−3.8 (4)
Cl2—C4—C5—C6180.0 (2)C18—C19—C20—O2179.7 (2)
C4—C5—C6—C1−0.4 (4)C18—C19—C20—C15−0.1 (4)
C4—C5—C6—C7176.1 (2)C16—C15—C20—O2−178.2 (2)
O1—C1—C6—C5−178.4 (2)C14—C15—C20—O21.8 (4)
C2—C1—C6—C52.0 (4)C16—C15—C20—C191.7 (4)
O1—C1—C6—C75.4 (4)C14—C15—C20—C19−178.4 (2)
C2—C1—C6—C7−174.2 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H1O3···Cl1i0.762.363.1093 (19)165
C12—H12A···Cl1ii0.932.813.725 (3)170
C14—H14A···Cl1ii0.932.723.606 (3)159
C2—H2A···Cg3iii0.933.023.890 (3)158
C16—H16A···Cg2iv0.933.353.880 (3)119
C18—H18A···Cg1iii0.932.963.640 (3)131

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2401).

References

  • Bruker (2005). APEX2 (Version 1.27), SAINT (Version 7.12A) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dixit, P. S. & Srinivasan, K. (1988). Inorg. Chem.27, 4507–4509.
  • Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Ibrahim, K. (2007). Acta Cryst. E63, m3193–m3194.
  • Glatzel, P., Bergmann, U., Yano, J., Visser, H., Robblee, J. H., Gu, W., de Groot, F. M. F., Christou, G., Pecoraro, V. L., Cramer, S. P. & Yachandra, V. K. (2004). J. Am. Chem. Soc.126, 9946–9959. [PubMed]
  • Habibi, M. H., Askari, E., Chantrapromma, S. & Fun, H.-K. (2007). Acta Cryst. E63, m2905–m2906.
  • Lu, Z., Yuan, M., Pan, F., Gao, S., Zhang, D. & Zhu, D. (2006). Inorg. Chem.45, 3538–3548. [PubMed]
  • Mitra, K., Biswas, S., Lucas, C. R. & Adhikary, B. (2006). Inorg. Chim. Acta, 359, 1997–2003.
  • Naskar, S., Biswas, S., Mishra, D., Adhikary, B., Falvello, L. R., Soler, T., Schwalbe, C. H. & Chattopadhyay, S. K. (2004). Inorg. Chim. Acta, 357, 4257–4264.
  • Sheldrick, G. M. (1998). SHELXTL Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Stallings, W. C., Pattridge, K. A., Strong, R. K. & Ludwig, M. L. (1985). J. Biol. Chem.260, 16424–16432. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography