metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 7| July 2010| Pages m734-m735

catena-Poly[[(4-methyl­benzoato-κO)manganese(II)]-μ-aqua-bis­­(μ-4-methyl­benzoato-κ2O:O′)[(4-methyl­benzoato-κO)manganese(II)]-bis­­(μ-N,N-di­ethyl­nicotinamide)-κ2N3:O;O:N3]

aDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey, bDepartment of Chemistry, Faculty of Science, Anadolu University, 26470 Yenibağlar, Eskişehir, Turkey, cDepartment of Physics, Karabük University, 78050, Karabük, Turkey, and dDepartment of Chemistry, Kafkas University, 63100 Kars, Turkey
*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 10 May 2010; accepted 27 May 2010; online 5 June 2010)

The asymmetric unit of the title complex, [Mn2(C8H7O2)4(C10H14N2O)2(H2O)]n, contains two crystallographically independent units. In each one, the MnII ions are bridged by two 4-methyl­benzoate (PMB) ligands and one water mol­ecule. In the crystal structure, each MnII ion is coordinated by three PMB ligands, one water mol­ecule and two symmetry-related N,N-diethyl­nicotinamide (DENA) ligands. Symmetry-related MnII ions are bridged by the N and O atoms of symmetry-related DENA ligands, forming polymeric chains parallel to [100]. The coord­ination environmnts for the MnII ions are slightly distorted octa­hedral. Intra­molecular O—H⋯O hydrogen bonds link bridging water mol­ecules to the carboxyl­ate O atoms of a neigh­boring polymeric chain. In the crystal structure, ππ contacts between benzene rings [centroid–centroid distance = 3.562 (1) Å] and weak C—H⋯π inter­actions are also observed.

Related literature

For applications of transition-metal complexes with bio­chem­ically relevant ligands in biological systems, see: Antolini et al. (1982[Antolini, L., Battaglia, L. P., Corradi, A. B., Marcotrigiano, G., Menabue, L., Pellacani, G. C. & Saladini, M. (1982). Inorg. Chem. 21, 1391-1395.]); Krishnamachari (1974[Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.]). For the use of 4-amino­benzoic acids in coordination chemistry, see: Amiraslanov et al. (1979[Amiraslanov, I. R., Mamedov, Kh. S., Movsumov, E. M., Musaev, F. N. & Nadzhafov, G. N. (1979). Zh. Strukt. Khim. 20, 1075-1080.]); Chen & Chen (2002[Chen, H. J. & Chen, X. M. (2002). Inorg. Chim. Acta, 329, 13-21.]); Hauptmann et al. (2000[Hauptmann, R., Kondo, M. & Kitagawa, S. (2000). Z. Kristallogr. New Cryst. Struct. 215, 169-172.]). N,N-Diethyl­nicotinamide (DENA) is an important respiratory stimulant, see: Bigoli et al. (1972[Bigoli, F., Braibanti, A., Pellinghelli, M. A. & Tiripicchio, A. (1972). Acta Cryst. B28, 962-966.]). For structure–function–coordination relationships of the aryl­carboxyl­ate ion in MnII complexes of benzoic acid derivatives, see: Adiwidjaja et al. (1978[Adiwidjaja, G., Rossmanith, E. & Küppers, H. (1978). Acta Cryst. B34, 3079-3083.]); Antsyshkina et al. (1980[Antsyshkina, A. S., Chiragov, F. M. & Poray-Koshits, M. A. (1980). Koord. Khim. 15, 1098-1103.]); Catterick et al. (1974[Catterick, J., Hursthouse, M. B., New, D. B. & Thorhton, P. (1974). J. Chem. Soc. Chem. Commun. pp. 843-844.]); Shnu­lin et al. (1981[Shnulin, A. N., Nadzhafov, G. N., Amiraslanov, I. R., Usubaliev, B. T. & Mamedov, Kh. S. (1981). Koord. Khim. 7, 1409-1416.]). For related structures, see: Hökelek et al. (2009a[Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2009a). Acta Cryst. E65, m747-m748.],b[Hökelek, T., Yılmaz, F., Tercan, B., Sertçelik, M. & Necefoğlu, H. (2009b). Acta Cryst. E65, m1399-m1400.]).

[Scheme 1]

Experimental

Crystal data
  • [Mn2(C8H7O2)4(C10H14N2O)2(H2O)]

  • Mr = 1024.90

  • Triclinic, [P \overline 1]

  • a = 10.5228 (2) Å

  • b = 19.1361 (3) Å

  • c = 26.6008 (4) Å

  • α = 70.537 (2)°

  • β = 78.836 (3)°

  • γ = 88.485 (3)°

  • V = 4950.63 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.57 mm−1

  • T = 100 K

  • 0.35 × 0.24 × 0.15 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.848, Tmax = 0.917

  • 87669 measured reflections

  • 24563 independent reflections

  • 17121 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.102

  • S = 1.02

  • 24563 reflections

  • 1275 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.51 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg5, Cg10 and Cg12 are the centroids of the C2–C7, N1/C33–C37, C78–C83 and N6/C90–C94 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
O9—H9A⋯O7 0.94 (3) 1.62 (3) 2.552 (2) 170 (3)
O9—H9B⋯O5 0.94 (2) 1.59 (2) 2.520 (2) 173 (3)
O22—H22A⋯O16 0.92 (3) 1.64 (3) 2.544 (2) 166 (2)
O22—H22B⋯O18 0.97 (4) 1.60 (4) 2.558 (2) 169 (3)
C52—H52ACg12i 0.96 2.87 3.782 (3) 160
C60—H60CCg1ii 0.96 2.99 3.841 (3) 149
C84—H84BCg10iii 0.96 2.88 3.609 (3) 134
C104—H10ECg5iv 0.96 2.82 3.709 (3) 155
Symmetry codes: (i) x+1, y, z; (ii) -x, -y, -z+1; (iii) -x+1, -y, -z+1; (iv) x-1, y, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Transition metal complexes with biochemicaly relevant ligands show interesting physical and/or chemical properties, through which they may find applications in biological systems (Antolini et al., 1982). Some benzoic acid derivatives, such as 4-aminobenzoic acid, have been extensively reported in coordination chemistry as bifunctional organic ligands due to the varieties of their coordination modes (Chen & Chen, 2002; Amiraslanov et al., 1979; Hauptmann et al., 2000). Nicotinamide (NA) is one form of niacin. A deficiency of this vitamin leads to loss of copper from the body, known as pellagra disease. Victims of pellagra show unusually high serum and urinary copper levels (Krishnamachari, 1974). The nicotinic acid derivative N,N-Diethylnicotinamide (DENA) is an important respiratory stimulant (Bigoli et al., 1972).

The structure-function-coordination relationships of arylcarboxylate ions in MnII complexes of benzoic acid derivatives may also change depending on the nature and position of the substituted groups on the benzene ring, the nature of the additional ligand molecule or solvent, and the pH and temperature of synthesis (Shnulin et al., 1981; Antsyshkina et al., 1980; Adiwidjaja et al., 1978). When pyridine and its derivatives are used instead of water molecules, the structure is completely different (Catterick et al., 1974). The title complex, (I), was synthesized and its crystal structure is reported herein.

The asymmetric unit of the title complex, (I), contains two crystallographically independent moieties. In each moiety, MnII ions are bridged by two 4-methylbenzoate (PMB) ligands and one water molecule. In the crystal structure of the title complex, each MnII ion is coordinated by three PMB ligands, one water molecule and two symmetry related DENA ligands. Symmetry related MnII ions are bridged by the N and O atoms of symmetry related DENA ligands forming polymeric chains (Fig. 1).

Coordination spheres around Mn1 and Mn2 (corresponding to Mn3 and Mn4 in the second moiety) are different. In the octahedron around Mn1 the nitrogen atom of a DENA ligand is in trans-position with respect to the bridging water ligand. The monodentate 4-methylbenzoate oxygen and another oxygen from the DENA ligand are trans to the bridging 4-methylbenzoate ligands. Around Mn2 bridging 4-methylbenzoate ligands are trans with respect to a DENA nitrogen atom and an oxygen from a another monodentate 4-methylbenzoate ligand.

Atoms (O2, O3, O8, O10), (O1, O4, O6, N1''), (O13, O15, O17, O21) and (O12, O14, O19, N6') in the equatorial planes around Mn1, Mn2, Mn3 and Mn4, respectively, form slightly distorted square-planar arrangements, while the slightly distorted octahedral coordinations are completed by the atoms (O9, N2), (O9, O11''), (O22, N5'') and (O20, O22) in the axial positions (Table 1 and Fig. 1) [symmetry codes:(') 1 + x, y, z, ('') x - 1, y, z]. The structures of similar MnII and Zn(II) polymeric complexes {[Mn(C11H14NO2)2(H2O)3].2H2O}n (Hökelek et al., 2009a) and [Zn(C8H5O3)2(C6H6N2O)]n (Hökelek et al., 2009b) have also been determined.

The average Mn—O bond length (Table 1) is 2.1699 (14) Å and Mn atoms are displaced out of the least-squares planes of the carboxylate groups: Mn1 atom for (O1/C1/O2), (O3/C9/O4) and (O7/C25/O8) by 0.3349 (3), 0.2642 (4) and -0.5844 (4) Å, respectively, Mn2 atom for (O1/C1/O2), (O3/C9/O4) and (O5/C17/O6) by -0.0412 (3), 0.4940 (4) and 0.1143 (3) Å, respectively, Mn3 atom for (O12/C53/O13), (O14/C61/O15) and (O16/C69/O17) by 0.3463 (4), -0.2062 (3) and 0.2611 (4) Å, respectively, and Mn4 atom for (O12/C53/O13), (O14/C61/O15) and (O18/C77/O19) by 0.6423 (4), 0.0305 (3) and 0.3320 (3) Å, respectively. The dihedral angles between the planar carboxylate groups and the adjacent benzene rings A (C2—C7), B (C10—C15), C (C18—C23), D (C26—C31), G (C54—C59), H (C62—C67), I (C70—C75) and J (C78—C83) are 13.35 (16), 10.82 (12), 7.48 (15), 7.33 (9), 11.86 (10), 11.42 (10), 6.68 (18) and 1.79 (11) °, respectively, while those between rings A, B, C, D, E (N1/C33—C37), F (N2/C38—C42) and G, H, I, J, K (N5/C86—C89), L (N6/C90—C94) are A/B = 64.86 (7), A/C = 35.09 (7), A/D = 63.93 (9), B/C = 83.44 (7), B/D = 22.10 (8), C/D = 87.56 (8), E/F = 33.93 (6) ° and G/H = 60.41 (6), G/I = 14.54 (8), G/J = 62.80 (7), H/I = 68.14 (7), H/J = 23.40 (7), I/J = 75.02 (8), K/L = 43.80 (8) °.

Intramolecular O—H···O hydrogen bonds (Table 1) link bridging water molecules to carboxylate O atoms of neighboring polymeric chains. In the crystal structure, ππ contacts between the benzene rings, Cg3—Cg3i with a centroid-centroid distance of 3.562 (1) Å [symmetry code: (i) -x, 1 - y, -z, where Cg3 is the centroid of the ring C (C18—C23)] and four weak C—H···π interactions are also observed (Table 1).

Related literature top

For applications of transition-metal complexes with biochemically relevant ligands in biological systems, see: Antolini et al. (1982); Krishnamachari (1974). For the use of 4-aminobenzoic acids in coordination chemistry, see: Amiraslanov et al. (1979); Chen & Chen (2002); Hauptmann et al. (2000). N,N-Diethylnicotinamide (DENA) is an important respiratory stimulant, see: Bigoli et al. (1972). For structure–function–coordination relationships of the arylcarboxylate ion in MnII complexes of benzoic acid derivatives, see: Adiwidjaja et al. (1978); Antsyshkina et al. (1980); Catterick et al. (1974); Shnulin et al. (1981). For related structures, see: Hökelek et al. (2009a,b).

Experimental top

The title compound was prepared by the reaction of MnSO4.H2O (0.84 g, 5 mmol) in H2O (10 ml) and DENA (1.78 g, 10 mmol) in H2O (10 ml) with sodium 4-methylbenzoate (1.58 g, 10 mmol) in H2O (150 ml). The mixture was filtered and set aside to crystallize at ambient temperature for one week, giving colorless single crystals (yield 2.05 g, 40.02 %).

Refinement top

Atoms H9A, H9B, H22A and H22B (for water molecules) were located in difference Fourier maps and refined isotropically, with restrain of O9—H9B = 0.937 (18) Å. [Uiso(H) = 0.046 (8), 0.069 (11), 0.035 (7) and 0.081 (12) Å2 for H9A, H9B, H22A and H22B, respectively]. The remaining H atoms were positioned geometrically with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 35% probability level. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity. Primed atoms are generated by the symmetry operators:(') 1 + x, y, z, ('') x - 1, y, z.
[Figure 2] Fig. 2. Part of the polymeric chains of the title compound.
catena-Poly[[(4-methylbenzoato-κO)manganese(II)]-µ-aqua- bis(µ-4-methylbenzoato-κ2O:O')[(4-methylbenzoato- κO)manganese(II)]-bis(µ-N,N-diethylnicotinamide)- κ2N3:O;O:N3] top
Crystal data top
[Mn2(C8H7O2)4(C10H14N2O)2(H2O)]Z = 4
Mr = 1024.90F(000) = 2144
Triclinic, P1Dx = 1.375 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.5228 (2) ÅCell parameters from 9867 reflections
b = 19.1361 (3) Åθ = 2.3–28.0°
c = 26.6008 (4) ŵ = 0.57 mm1
α = 70.537 (2)°T = 100 K
β = 78.836 (3)°Block, colorless
γ = 88.485 (3)°0.35 × 0.24 × 0.15 mm
V = 4950.63 (17) Å3
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
24563 independent reflections
Radiation source: fine-focus sealed tube17121 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ϕ and ω scansθmax = 28.4°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1414
Tmin = 0.848, Tmax = 0.917k = 2525
87669 measured reflectionsl = 3535
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0376P)2 + 2.5004P]
where P = (Fo2 + 2Fc2)/3
24563 reflections(Δ/σ)max = 0.001
1275 parametersΔρmax = 0.40 e Å3
1 restraintΔρmin = 0.51 e Å3
Crystal data top
[Mn2(C8H7O2)4(C10H14N2O)2(H2O)]γ = 88.485 (3)°
Mr = 1024.90V = 4950.63 (17) Å3
Triclinic, P1Z = 4
a = 10.5228 (2) ÅMo Kα radiation
b = 19.1361 (3) ŵ = 0.57 mm1
c = 26.6008 (4) ÅT = 100 K
α = 70.537 (2)°0.35 × 0.24 × 0.15 mm
β = 78.836 (3)°
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
24563 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
17121 reflections with I > 2σ(I)
Tmin = 0.848, Tmax = 0.917Rint = 0.049
87669 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0421 restraint
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.40 e Å3
24563 reflectionsΔρmin = 0.51 e Å3
1275 parameters
Special details top

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
Mn10.29102 (3)0.092307 (17)0.156751 (12)0.01457 (7)
Mn20.02201 (3)0.133661 (17)0.112030 (12)0.01425 (7)
Mn30.20220 (3)0.461244 (17)0.326281 (12)0.01420 (7)
Mn40.51449 (3)0.407633 (17)0.366892 (12)0.01429 (7)
O10.00798 (14)0.01586 (8)0.14766 (6)0.0216 (3)
O20.19077 (14)0.00928 (8)0.16623 (6)0.0215 (3)
O30.32961 (14)0.13578 (8)0.06967 (6)0.0203 (3)
O40.13544 (14)0.15161 (8)0.04538 (6)0.0210 (3)
O50.10170 (14)0.28937 (8)0.11920 (6)0.0223 (3)
O60.05798 (14)0.25125 (8)0.08837 (6)0.0191 (3)
O70.05950 (15)0.08986 (9)0.26520 (6)0.0245 (3)
O80.26278 (14)0.05493 (9)0.24495 (6)0.0220 (3)
O90.11046 (14)0.15084 (8)0.16200 (6)0.0164 (3)
H9A0.085 (3)0.1322 (15)0.1999 (12)0.046 (8)*
H9B0.112 (3)0.2027 (10)0.1476 (13)0.069 (11)*
O100.40261 (14)0.18976 (8)0.15298 (6)0.0210 (3)
O110.15129 (14)0.11306 (8)0.06165 (6)0.0183 (3)
O120.35950 (14)0.37541 (9)0.43431 (6)0.0217 (3)
O130.16363 (14)0.39528 (8)0.41208 (6)0.0193 (3)
O140.49611 (14)0.52498 (8)0.34726 (6)0.0222 (3)
O150.30051 (14)0.55792 (8)0.32796 (6)0.0205 (3)
O160.42449 (14)0.47310 (9)0.21309 (6)0.0236 (3)
O170.22779 (14)0.51251 (8)0.23789 (6)0.0217 (3)
O180.38854 (15)0.25966 (8)0.35204 (6)0.0243 (4)
O190.55809 (14)0.29317 (8)0.37939 (6)0.0207 (3)
O200.65101 (13)0.41069 (8)0.41920 (6)0.0187 (3)
O210.08786 (14)0.37412 (8)0.31793 (6)0.0217 (3)
O220.37934 (14)0.40100 (9)0.31456 (6)0.0160 (3)
H22A0.406 (2)0.4217 (14)0.2775 (11)0.035 (7)*
H22B0.374 (3)0.347 (2)0.3269 (14)0.081 (12)*
N10.20574 (17)0.12154 (10)0.17872 (7)0.0171 (4)
N20.47393 (17)0.02732 (10)0.14640 (7)0.0172 (4)
N30.83418 (17)0.05090 (10)0.00421 (7)0.0181 (4)
N40.45429 (17)0.27187 (10)0.19043 (7)0.0195 (4)
N50.01818 (16)0.51791 (10)0.35032 (7)0.0166 (4)
N60.68991 (16)0.43439 (9)0.29721 (7)0.0168 (4)
N70.65443 (17)0.44424 (10)0.49232 (7)0.0193 (4)
N80.03462 (17)0.29462 (10)0.27868 (7)0.0179 (4)
C10.0784 (2)0.02758 (12)0.16489 (8)0.0169 (4)
C20.0427 (2)0.10932 (11)0.18415 (8)0.0169 (4)
C30.0853 (2)0.13269 (12)0.19115 (8)0.0186 (4)
H30.14950.09800.18700.022*
C40.1182 (2)0.20697 (12)0.20415 (9)0.0208 (5)
H40.20450.22170.20880.025*
C50.0241 (2)0.25999 (12)0.21033 (9)0.0208 (5)
C60.1028 (2)0.23687 (12)0.20604 (9)0.0216 (5)
H60.16620.27180.21200.026*
C70.1363 (2)0.16242 (12)0.19306 (9)0.0201 (5)
H70.22180.14790.19030.024*
C80.0587 (2)0.33925 (12)0.21777 (10)0.0281 (5)
H8A0.00820.37070.23160.042*
H8B0.06670.34310.18340.042*
H8C0.13950.35450.24310.042*
C90.2572 (2)0.15832 (11)0.03538 (8)0.0165 (4)
C100.3218 (2)0.19464 (11)0.02273 (8)0.0171 (4)
C110.2489 (2)0.23152 (12)0.06148 (9)0.0210 (5)
H110.15930.23210.05130.025*
C120.3087 (2)0.26728 (13)0.11504 (9)0.0248 (5)
H120.25870.29200.14030.030*
C130.4422 (2)0.26688 (12)0.13162 (9)0.0233 (5)
C140.5145 (2)0.22896 (13)0.09326 (9)0.0238 (5)
H140.60370.22700.10370.029*
C150.4551 (2)0.19386 (12)0.03941 (9)0.0201 (5)
H150.50540.16950.01420.024*
C160.5066 (3)0.30636 (14)0.18978 (9)0.0347 (6)
H16A0.44320.33280.20970.052*
H16B0.54470.27080.20590.052*
H16C0.57280.34070.19090.052*
C170.0039 (2)0.30073 (11)0.09722 (8)0.0171 (4)
C180.0438 (2)0.37802 (12)0.08131 (8)0.0178 (4)
C190.1414 (2)0.39756 (13)0.05159 (10)0.0274 (5)
H190.17820.36220.04120.033*
C200.1848 (2)0.46928 (13)0.03717 (10)0.0298 (5)
H200.25040.48130.01720.036*
C210.1322 (2)0.52330 (13)0.05200 (9)0.0260 (5)
C220.0330 (2)0.50357 (13)0.08122 (10)0.0281 (5)
H220.00500.53910.09110.034*
C230.0104 (2)0.43205 (12)0.09590 (9)0.0231 (5)
H230.07640.42000.11570.028*
C240.1783 (2)0.60127 (13)0.03638 (11)0.0342 (6)
H24A0.10750.63520.03110.051*
H24B0.24630.60570.06480.051*
H24C0.21050.61270.00330.051*
C250.1568 (2)0.05343 (12)0.27750 (9)0.0187 (4)
C260.1452 (2)0.00386 (12)0.33574 (9)0.0204 (5)
C270.0350 (2)0.00399 (14)0.37437 (9)0.0300 (5)
H270.03040.03620.36450.036*
C280.0225 (3)0.04345 (15)0.42726 (10)0.0391 (7)
H280.05090.04190.45270.047*
C290.1168 (3)0.09347 (14)0.44339 (10)0.0361 (7)
C300.2254 (3)0.09338 (14)0.40479 (11)0.0367 (7)
H300.29000.12640.41460.044*
C310.2404 (2)0.04492 (13)0.35141 (10)0.0281 (5)
H310.31500.04550.32630.034*
C320.0996 (3)0.14617 (17)0.50102 (11)0.0553 (9)
H32A0.08160.11870.52570.083*
H32B0.17750.17260.50600.083*
H32C0.02860.18080.50800.083*
C330.2241 (2)0.07042 (11)0.22842 (9)0.0183 (4)
H330.15660.03980.23830.022*
C340.3392 (2)0.06135 (12)0.26569 (9)0.0214 (5)
H340.34810.02560.30000.026*
C350.4409 (2)0.10575 (12)0.25143 (9)0.0199 (5)
H350.51980.09970.27560.024*
C360.42287 (19)0.15955 (11)0.20030 (8)0.0155 (4)
C370.30381 (19)0.16563 (11)0.16559 (8)0.0161 (4)
H370.29140.20210.13150.019*
C380.4733 (2)0.04641 (12)0.17108 (9)0.0190 (4)
H380.40310.06930.19850.023*
C390.5722 (2)0.08989 (12)0.15759 (9)0.0213 (5)
H390.56820.14080.17560.026*
C400.6768 (2)0.05651 (12)0.11698 (9)0.0211 (5)
H400.74330.08480.10660.025*
C410.6813 (2)0.02013 (11)0.09173 (8)0.0164 (4)
C420.5773 (2)0.05918 (11)0.10813 (8)0.0160 (4)
H420.57990.11040.09150.019*
C430.79495 (19)0.06378 (11)0.05116 (8)0.0159 (4)
C440.7643 (2)0.00135 (13)0.01427 (9)0.0240 (5)
H44A0.72130.03880.01730.029*
H44B0.82670.02030.03620.029*
C450.6646 (2)0.03952 (14)0.04705 (10)0.0317 (6)
H45A0.62490.00460.05870.047*
H45B0.70610.07960.07830.047*
H45C0.59950.05860.02500.047*
C460.9449 (2)0.09632 (12)0.03440 (9)0.0228 (5)
H46A0.97680.07360.06180.027*
H46B1.01400.09680.01510.027*
C470.9114 (2)0.17535 (13)0.06227 (10)0.0287 (5)
H47A0.98430.20080.08960.043*
H47B0.89050.20020.03590.043*
H47C0.83830.17530.07890.043*
C480.47036 (19)0.20863 (12)0.18015 (8)0.0162 (4)
C490.3529 (2)0.32107 (13)0.16928 (10)0.0244 (5)
H49A0.33390.35520.18950.029*
H49B0.27450.29130.17560.029*
C500.3893 (2)0.36527 (14)0.10934 (10)0.0342 (6)
H50A0.32430.40050.09930.051*
H50B0.39540.33230.08860.051*
H50C0.47140.39110.10200.051*
C510.5357 (2)0.29619 (13)0.22146 (9)0.0248 (5)
H51A0.57110.25290.24480.030*
H51B0.48160.31970.24460.030*
C520.6457 (2)0.34963 (14)0.18583 (11)0.0342 (6)
H52A0.69610.36230.20820.051*
H52B0.61130.39370.16390.051*
H52C0.69970.32680.16270.051*
C530.2385 (2)0.36444 (11)0.44399 (8)0.0167 (4)
C540.1792 (2)0.31129 (11)0.49916 (8)0.0170 (4)
C550.0468 (2)0.30495 (12)0.51870 (9)0.0204 (5)
H550.00820.33270.49680.024*
C560.0045 (2)0.25787 (13)0.57045 (9)0.0240 (5)
H560.09380.25500.58290.029*
C570.0741 (2)0.21472 (12)0.60428 (9)0.0238 (5)
C580.2070 (2)0.21989 (12)0.58382 (9)0.0232 (5)
H580.26180.19080.60520.028*
C590.2591 (2)0.26750 (12)0.53229 (9)0.0219 (5)
H590.34830.27030.51960.026*
C600.0182 (3)0.16500 (14)0.66114 (10)0.0340 (6)
H60A0.06530.12030.66960.051*
H60B0.07130.15290.66370.051*
H60C0.02500.19010.68640.051*
C610.4106 (2)0.57161 (12)0.33415 (8)0.0165 (4)
C620.4477 (2)0.65083 (11)0.32589 (8)0.0158 (4)
C630.3573 (2)0.70589 (12)0.32052 (9)0.0202 (5)
H630.27110.69410.32200.024*
C640.3946 (2)0.77828 (12)0.31296 (9)0.0220 (5)
H640.33300.81450.30950.026*
C650.5228 (2)0.79759 (12)0.31052 (9)0.0200 (5)
C660.6129 (2)0.74237 (12)0.31522 (9)0.0202 (5)
H660.69920.75410.31340.024*
C670.5759 (2)0.67020 (12)0.32261 (8)0.0183 (4)
H670.63780.63420.32540.022*
C680.5636 (2)0.87545 (12)0.30437 (10)0.0278 (5)
H68A0.51720.91040.28000.042*
H68B0.65500.88350.29000.042*
H68C0.54460.88210.33920.042*
C690.3274 (2)0.51141 (12)0.20306 (9)0.0179 (4)
C700.3331 (2)0.56018 (12)0.14482 (8)0.0190 (4)
C710.2283 (2)0.60070 (12)0.12891 (9)0.0229 (5)
H710.15150.59650.15400.027*
C720.2373 (2)0.64770 (13)0.07557 (10)0.0272 (5)
H720.16540.67380.06540.033*
C730.3505 (2)0.65661 (13)0.03725 (9)0.0272 (5)
C740.4538 (2)0.61449 (14)0.05329 (9)0.0304 (6)
H740.53020.61820.02800.036*
C750.4457 (2)0.56714 (13)0.10592 (9)0.0255 (5)
H750.51660.53950.11550.031*
C760.3644 (3)0.71158 (14)0.01987 (10)0.0355 (6)
H76A0.44120.74260.02830.053*
H76B0.29000.74180.02230.053*
H76C0.37090.68520.04520.053*
C770.4867 (2)0.24556 (12)0.37353 (8)0.0185 (4)
C780.5223 (2)0.16569 (12)0.39390 (9)0.0198 (5)
C790.4467 (2)0.11043 (12)0.38984 (9)0.0245 (5)
H790.37360.12280.37440.029*
C800.4790 (2)0.03679 (13)0.40862 (10)0.0287 (5)
H800.42630.00040.40600.034*
C810.5883 (2)0.01624 (13)0.43122 (10)0.0277 (5)
C820.6634 (3)0.07218 (14)0.43503 (11)0.0346 (6)
H820.73680.06000.45030.042*
C830.6311 (2)0.14594 (13)0.41647 (10)0.0289 (5)
H830.68330.18240.41930.035*
C840.6237 (3)0.06375 (13)0.45167 (11)0.0393 (7)
H84A0.55810.09470.44810.059*
H84B0.63000.07730.48920.059*
H84C0.70550.07020.43070.059*
C850.08494 (19)0.47597 (12)0.38283 (8)0.0156 (4)
H850.08350.42500.38990.019*
C860.19401 (19)0.50452 (12)0.40655 (8)0.0159 (4)
C870.1961 (2)0.58115 (12)0.39485 (9)0.0196 (5)
H870.26710.60260.40990.023*
C880.0908 (2)0.62472 (12)0.36043 (9)0.0211 (5)
H880.09060.67600.35150.025*
C890.0139 (2)0.59133 (12)0.33947 (9)0.0186 (4)
H890.08480.62110.31670.022*
C900.7032 (2)0.48943 (11)0.24927 (8)0.0180 (4)
H900.63230.51810.24120.022*
C910.8177 (2)0.50526 (12)0.21137 (9)0.0211 (5)
H910.82270.54340.17830.025*
C920.9247 (2)0.46414 (12)0.22288 (9)0.0195 (4)
H921.00360.47520.19850.023*
C930.9114 (2)0.40577 (11)0.27179 (8)0.0159 (4)
C940.79259 (19)0.39322 (11)0.30731 (8)0.0160 (4)
H940.78380.35400.34000.019*
C950.69637 (19)0.45079 (12)0.44036 (8)0.0160 (4)
C960.7140 (2)0.48486 (13)0.52104 (9)0.0246 (5)
H96A0.64950.48910.55120.030*
H96B0.74000.53460.49630.030*
C970.8309 (2)0.44791 (14)0.54251 (10)0.0290 (5)
H97A0.86340.47590.56170.044*
H97B0.89720.44600.51270.044*
H97C0.80620.39840.56680.044*
C980.5546 (2)0.38594 (13)0.52469 (9)0.0257 (5)
H98A0.48570.38880.50460.031*
H98B0.51750.39500.55820.031*
C990.6063 (2)0.30848 (14)0.53846 (10)0.0317 (6)
H99A0.53890.27320.56200.048*
H99B0.67790.30610.55640.048*
H99C0.63480.29710.50560.048*
C1000.01980 (19)0.35729 (12)0.29004 (8)0.0156 (4)
C1010.1292 (2)0.24234 (12)0.30289 (9)0.0228 (5)
H10A0.21070.26910.29700.027*
H10B0.14460.20560.28480.027*
C1020.0828 (2)0.20352 (14)0.36308 (10)0.0324 (6)
H10H0.14440.16780.37680.049*
H10I0.00030.17870.36920.049*
H10J0.07420.23930.38150.049*
C1030.0447 (2)0.27293 (13)0.24597 (9)0.0232 (5)
H10C0.01030.25050.22230.028*
H10D0.07900.31710.22310.028*
C1040.1561 (2)0.21903 (13)0.27990 (10)0.0298 (6)
H10E0.20540.20810.25640.045*
H10F0.21090.24070.30360.045*
H10G0.12270.17410.30120.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.01369 (16)0.01606 (16)0.01613 (16)0.00008 (12)0.00361 (12)0.00779 (13)
Mn20.01361 (16)0.01591 (16)0.01577 (16)0.00055 (12)0.00323 (12)0.00843 (13)
Mn30.01195 (15)0.01724 (16)0.01632 (16)0.00047 (12)0.00281 (12)0.00939 (13)
Mn40.01224 (16)0.01742 (16)0.01566 (16)0.00045 (12)0.00275 (12)0.00872 (13)
O10.0193 (8)0.0177 (8)0.0293 (9)0.0016 (6)0.0071 (7)0.0088 (7)
O20.0157 (8)0.0183 (8)0.0322 (9)0.0017 (6)0.0047 (7)0.0106 (7)
O30.0197 (8)0.0242 (8)0.0175 (8)0.0028 (6)0.0042 (6)0.0075 (7)
O40.0171 (8)0.0281 (9)0.0206 (8)0.0017 (7)0.0013 (6)0.0129 (7)
O50.0234 (8)0.0175 (8)0.0283 (9)0.0012 (6)0.0121 (7)0.0069 (7)
O60.0197 (8)0.0154 (7)0.0243 (8)0.0007 (6)0.0073 (6)0.0078 (6)
O70.0248 (9)0.0285 (9)0.0197 (8)0.0076 (7)0.0033 (7)0.0087 (7)
O80.0181 (8)0.0301 (9)0.0177 (8)0.0011 (7)0.0040 (6)0.0078 (7)
O90.0179 (8)0.0170 (8)0.0169 (8)0.0024 (6)0.0051 (6)0.0084 (7)
O100.0223 (8)0.0192 (8)0.0252 (8)0.0021 (6)0.0095 (7)0.0093 (7)
O110.0180 (8)0.0212 (8)0.0196 (8)0.0012 (6)0.0056 (6)0.0108 (6)
O120.0158 (8)0.0331 (9)0.0180 (8)0.0028 (7)0.0012 (6)0.0117 (7)
O130.0181 (8)0.0220 (8)0.0177 (8)0.0013 (6)0.0028 (6)0.0072 (6)
O140.0190 (8)0.0193 (8)0.0323 (9)0.0023 (6)0.0055 (7)0.0139 (7)
O150.0156 (8)0.0210 (8)0.0284 (9)0.0019 (6)0.0032 (6)0.0133 (7)
O160.0215 (8)0.0279 (9)0.0193 (8)0.0078 (7)0.0035 (6)0.0061 (7)
O170.0189 (8)0.0281 (9)0.0181 (8)0.0040 (7)0.0021 (6)0.0089 (7)
O180.0247 (9)0.0191 (8)0.0307 (9)0.0009 (7)0.0136 (7)0.0056 (7)
O190.0186 (8)0.0177 (8)0.0279 (9)0.0000 (6)0.0067 (6)0.0093 (7)
O200.0155 (7)0.0256 (8)0.0188 (8)0.0005 (6)0.0053 (6)0.0111 (7)
O210.0201 (8)0.0226 (8)0.0294 (9)0.0015 (6)0.0091 (7)0.0153 (7)
O220.0171 (8)0.0180 (8)0.0151 (8)0.0023 (6)0.0037 (6)0.0081 (6)
N10.0189 (9)0.0196 (9)0.0170 (9)0.0013 (7)0.0048 (7)0.0107 (8)
N20.0170 (9)0.0184 (9)0.0182 (9)0.0009 (7)0.0062 (7)0.0071 (8)
N30.0197 (9)0.0193 (9)0.0183 (9)0.0004 (7)0.0038 (7)0.0103 (8)
N40.0161 (9)0.0232 (10)0.0257 (10)0.0042 (7)0.0068 (8)0.0155 (8)
N50.0156 (9)0.0197 (9)0.0169 (9)0.0011 (7)0.0047 (7)0.0086 (7)
N60.0168 (9)0.0179 (9)0.0179 (9)0.0002 (7)0.0033 (7)0.0091 (7)
N70.0160 (9)0.0274 (10)0.0171 (9)0.0022 (8)0.0024 (7)0.0115 (8)
N80.0173 (9)0.0200 (9)0.0223 (10)0.0030 (7)0.0063 (7)0.0135 (8)
C10.0172 (11)0.0189 (11)0.0167 (10)0.0009 (8)0.0019 (8)0.0093 (9)
C20.0195 (11)0.0170 (10)0.0148 (10)0.0006 (8)0.0033 (8)0.0062 (9)
C30.0170 (11)0.0205 (11)0.0185 (11)0.0001 (9)0.0018 (8)0.0075 (9)
C40.0183 (11)0.0219 (11)0.0220 (11)0.0048 (9)0.0015 (9)0.0082 (9)
C50.0283 (12)0.0163 (11)0.0179 (11)0.0035 (9)0.0045 (9)0.0058 (9)
C60.0230 (12)0.0196 (11)0.0221 (12)0.0040 (9)0.0056 (9)0.0062 (9)
C70.0185 (11)0.0197 (11)0.0229 (11)0.0016 (9)0.0048 (9)0.0077 (9)
C80.0353 (14)0.0197 (12)0.0301 (13)0.0025 (10)0.0080 (11)0.0084 (10)
C90.0199 (11)0.0148 (10)0.0185 (11)0.0004 (8)0.0028 (9)0.0109 (9)
C100.0220 (11)0.0146 (10)0.0170 (10)0.0008 (8)0.0035 (9)0.0084 (9)
C110.0197 (11)0.0248 (12)0.0212 (11)0.0034 (9)0.0059 (9)0.0105 (10)
C120.0327 (13)0.0243 (12)0.0225 (12)0.0068 (10)0.0126 (10)0.0108 (10)
C130.0340 (13)0.0201 (11)0.0171 (11)0.0031 (10)0.0027 (10)0.0090 (9)
C140.0184 (11)0.0319 (13)0.0216 (12)0.0036 (10)0.0006 (9)0.0110 (10)
C150.0195 (11)0.0246 (12)0.0177 (11)0.0003 (9)0.0037 (9)0.0090 (9)
C160.0463 (16)0.0360 (15)0.0188 (12)0.0075 (12)0.0016 (11)0.0073 (11)
C170.0186 (11)0.0161 (10)0.0151 (10)0.0006 (8)0.0008 (8)0.0047 (8)
C180.0174 (11)0.0185 (11)0.0164 (10)0.0002 (9)0.0000 (8)0.0061 (9)
C190.0270 (13)0.0223 (12)0.0368 (14)0.0034 (10)0.0125 (11)0.0116 (11)
C200.0261 (13)0.0277 (13)0.0364 (14)0.0074 (10)0.0114 (11)0.0093 (11)
C210.0273 (13)0.0214 (12)0.0230 (12)0.0048 (10)0.0050 (10)0.0049 (10)
C220.0346 (14)0.0213 (12)0.0307 (13)0.0005 (10)0.0039 (11)0.0131 (11)
C230.0248 (12)0.0210 (11)0.0254 (12)0.0010 (9)0.0069 (10)0.0092 (10)
C240.0328 (14)0.0240 (13)0.0397 (15)0.0092 (11)0.0024 (12)0.0088 (12)
C250.0224 (12)0.0182 (11)0.0190 (11)0.0020 (9)0.0046 (9)0.0102 (9)
C260.0238 (12)0.0188 (11)0.0194 (11)0.0049 (9)0.0063 (9)0.0058 (9)
C270.0369 (15)0.0299 (13)0.0223 (12)0.0016 (11)0.0015 (11)0.0100 (11)
C280.0489 (18)0.0406 (16)0.0227 (13)0.0093 (13)0.0027 (12)0.0087 (12)
C290.0511 (18)0.0326 (14)0.0220 (13)0.0196 (13)0.0120 (12)0.0015 (11)
C300.0416 (16)0.0293 (14)0.0371 (15)0.0065 (12)0.0240 (13)0.0015 (12)
C310.0267 (13)0.0288 (13)0.0284 (13)0.0056 (10)0.0084 (10)0.0068 (11)
C320.088 (3)0.0488 (19)0.0237 (15)0.0261 (18)0.0187 (15)0.0022 (13)
C330.0187 (11)0.0153 (10)0.0232 (11)0.0000 (8)0.0066 (9)0.0080 (9)
C340.0259 (12)0.0164 (11)0.0196 (11)0.0045 (9)0.0017 (9)0.0042 (9)
C350.0179 (11)0.0219 (11)0.0203 (11)0.0041 (9)0.0011 (9)0.0101 (9)
C360.0149 (10)0.0180 (10)0.0183 (11)0.0024 (8)0.0037 (8)0.0117 (9)
C370.0179 (11)0.0173 (10)0.0155 (10)0.0008 (8)0.0047 (8)0.0077 (9)
C380.0173 (11)0.0193 (11)0.0201 (11)0.0013 (9)0.0060 (9)0.0047 (9)
C390.0238 (12)0.0149 (10)0.0243 (12)0.0008 (9)0.0080 (9)0.0036 (9)
C400.0226 (12)0.0207 (11)0.0245 (12)0.0063 (9)0.0087 (9)0.0118 (10)
C410.0176 (11)0.0193 (11)0.0168 (10)0.0005 (8)0.0066 (8)0.0101 (9)
C420.0192 (11)0.0156 (10)0.0160 (10)0.0006 (8)0.0070 (8)0.0068 (8)
C430.0140 (10)0.0204 (11)0.0163 (10)0.0041 (8)0.0058 (8)0.0087 (9)
C440.0320 (13)0.0257 (12)0.0222 (12)0.0028 (10)0.0078 (10)0.0169 (10)
C450.0306 (14)0.0350 (14)0.0400 (15)0.0027 (11)0.0156 (12)0.0218 (12)
C460.0230 (12)0.0285 (12)0.0178 (11)0.0020 (10)0.0003 (9)0.0114 (10)
C470.0297 (13)0.0298 (13)0.0243 (12)0.0040 (11)0.0060 (10)0.0053 (11)
C480.0135 (10)0.0199 (11)0.0149 (10)0.0014 (8)0.0004 (8)0.0072 (9)
C490.0200 (12)0.0258 (12)0.0352 (13)0.0069 (10)0.0102 (10)0.0183 (11)
C500.0302 (14)0.0300 (14)0.0400 (15)0.0003 (11)0.0114 (12)0.0057 (12)
C510.0236 (12)0.0309 (13)0.0333 (13)0.0088 (10)0.0118 (10)0.0257 (11)
C520.0260 (13)0.0370 (15)0.0519 (17)0.0011 (11)0.0151 (12)0.0267 (13)
C530.0190 (11)0.0179 (11)0.0168 (10)0.0003 (9)0.0021 (8)0.0111 (9)
C540.0194 (11)0.0163 (10)0.0187 (11)0.0006 (8)0.0044 (8)0.0102 (9)
C550.0193 (11)0.0214 (11)0.0213 (11)0.0008 (9)0.0043 (9)0.0080 (9)
C560.0195 (12)0.0270 (12)0.0254 (12)0.0048 (10)0.0004 (9)0.0103 (10)
C570.0339 (14)0.0190 (11)0.0200 (11)0.0076 (10)0.0040 (10)0.0086 (9)
C580.0296 (13)0.0197 (11)0.0235 (12)0.0037 (10)0.0106 (10)0.0085 (10)
C590.0201 (11)0.0239 (12)0.0244 (12)0.0015 (9)0.0052 (9)0.0112 (10)
C600.0466 (16)0.0286 (13)0.0246 (13)0.0117 (12)0.0068 (11)0.0051 (11)
C610.0168 (11)0.0197 (11)0.0154 (10)0.0009 (8)0.0000 (8)0.0109 (9)
C620.0180 (11)0.0172 (10)0.0134 (10)0.0001 (8)0.0020 (8)0.0073 (8)
C630.0150 (11)0.0239 (11)0.0236 (12)0.0016 (9)0.0037 (9)0.0103 (10)
C640.0215 (12)0.0193 (11)0.0268 (12)0.0046 (9)0.0061 (9)0.0092 (10)
C650.0228 (12)0.0199 (11)0.0175 (11)0.0035 (9)0.0030 (9)0.0067 (9)
C660.0180 (11)0.0219 (11)0.0211 (11)0.0060 (9)0.0038 (9)0.0073 (9)
C670.0182 (11)0.0205 (11)0.0171 (11)0.0020 (9)0.0040 (8)0.0072 (9)
C680.0296 (13)0.0200 (12)0.0337 (14)0.0031 (10)0.0081 (11)0.0075 (10)
C690.0189 (11)0.0180 (11)0.0189 (11)0.0012 (9)0.0038 (9)0.0087 (9)
C700.0237 (12)0.0177 (11)0.0168 (11)0.0010 (9)0.0052 (9)0.0067 (9)
C710.0212 (12)0.0216 (11)0.0263 (12)0.0016 (9)0.0062 (9)0.0078 (10)
C720.0311 (13)0.0212 (12)0.0306 (13)0.0039 (10)0.0163 (11)0.0049 (10)
C730.0383 (15)0.0231 (12)0.0214 (12)0.0035 (11)0.0109 (11)0.0057 (10)
C740.0307 (14)0.0387 (15)0.0187 (12)0.0002 (11)0.0013 (10)0.0074 (11)
C750.0269 (13)0.0274 (13)0.0213 (12)0.0055 (10)0.0062 (10)0.0064 (10)
C760.0464 (17)0.0319 (14)0.0253 (13)0.0074 (12)0.0144 (12)0.0009 (11)
C770.0182 (11)0.0186 (11)0.0171 (11)0.0011 (9)0.0011 (8)0.0053 (9)
C780.0223 (12)0.0179 (11)0.0196 (11)0.0002 (9)0.0029 (9)0.0076 (9)
C790.0273 (13)0.0228 (12)0.0249 (12)0.0016 (10)0.0067 (10)0.0089 (10)
C800.0380 (15)0.0194 (12)0.0311 (13)0.0035 (10)0.0069 (11)0.0111 (10)
C810.0354 (14)0.0200 (12)0.0262 (13)0.0021 (10)0.0011 (11)0.0085 (10)
C820.0329 (15)0.0267 (13)0.0471 (16)0.0079 (11)0.0181 (12)0.0107 (12)
C830.0296 (13)0.0205 (12)0.0397 (15)0.0007 (10)0.0135 (11)0.0103 (11)
C840.0519 (18)0.0225 (13)0.0447 (17)0.0081 (12)0.0090 (14)0.0136 (12)
C850.0170 (11)0.0172 (10)0.0163 (10)0.0006 (8)0.0051 (8)0.0093 (9)
C860.0136 (10)0.0228 (11)0.0160 (10)0.0022 (8)0.0057 (8)0.0113 (9)
C870.0174 (11)0.0244 (12)0.0233 (11)0.0071 (9)0.0074 (9)0.0149 (10)
C880.0216 (12)0.0155 (11)0.0303 (12)0.0032 (9)0.0105 (10)0.0101 (10)
C890.0174 (11)0.0186 (11)0.0215 (11)0.0015 (9)0.0068 (9)0.0070 (9)
C900.0186 (11)0.0170 (11)0.0217 (11)0.0016 (9)0.0056 (9)0.0102 (9)
C910.0239 (12)0.0181 (11)0.0193 (11)0.0030 (9)0.0025 (9)0.0042 (9)
C920.0151 (11)0.0205 (11)0.0222 (11)0.0043 (9)0.0014 (9)0.0085 (9)
C930.0167 (10)0.0170 (10)0.0196 (11)0.0004 (8)0.0040 (8)0.0133 (9)
C940.0170 (11)0.0170 (10)0.0159 (10)0.0002 (8)0.0027 (8)0.0081 (9)
C950.0119 (10)0.0218 (11)0.0176 (10)0.0045 (8)0.0046 (8)0.0102 (9)
C960.0280 (13)0.0331 (13)0.0196 (11)0.0038 (10)0.0052 (9)0.0176 (10)
C970.0289 (13)0.0365 (14)0.0314 (13)0.0054 (11)0.0134 (11)0.0203 (12)
C980.0191 (12)0.0404 (14)0.0173 (11)0.0013 (10)0.0013 (9)0.0101 (10)
C990.0274 (13)0.0345 (14)0.0287 (13)0.0051 (11)0.0086 (11)0.0024 (11)
C1000.0110 (10)0.0210 (11)0.0152 (10)0.0016 (8)0.0013 (8)0.0087 (9)
C1010.0208 (12)0.0235 (12)0.0315 (13)0.0064 (9)0.0113 (10)0.0157 (10)
C1020.0308 (14)0.0304 (14)0.0337 (14)0.0001 (11)0.0121 (11)0.0045 (11)
C1030.0268 (12)0.0272 (12)0.0282 (12)0.0072 (10)0.0134 (10)0.0217 (10)
C1040.0266 (13)0.0288 (13)0.0458 (15)0.0027 (10)0.0162 (11)0.0228 (12)
Geometric parameters (Å, º) top
Mn1—O22.1528 (14)C41—C401.393 (3)
Mn1—O32.1429 (15)C41—C421.391 (3)
Mn1—O82.1743 (15)C41—C431.498 (3)
Mn1—O92.1848 (15)C42—N21.336 (3)
Mn1—O102.1936 (14)C42—H420.9300
Mn1—N22.2854 (18)C43—O11ii1.246 (2)
Mn2—O12.1482 (15)C44—C451.511 (3)
Mn2—O42.1197 (15)C44—H44A0.9700
Mn2—O62.1694 (14)C44—H44B0.9700
Mn2—O92.2026 (14)C45—H45A0.9600
Mn2—O112.2109 (13)C45—H45B0.9600
Mn2—N12.3152 (18)C45—H45C0.9600
Mn3—O132.1716 (14)C46—C471.512 (3)
Mn3—O152.1608 (14)C46—H46A0.9700
Mn3—O172.1898 (15)C46—H46B0.9700
Mn3—O212.1755 (14)C47—H47A0.9600
Mn3—O222.1913 (15)C47—H47B0.9600
Mn3—N52.2817 (17)C47—H47C0.9600
Mn4—O122.1071 (15)C48—O101.244 (2)
Mn4—O142.1419 (15)C48—C36ii1.508 (3)
Mn4—O192.1540 (15)C49—C501.512 (3)
Mn4—O202.1990 (13)C49—H49A0.9700
Mn4—O222.2069 (14)C49—H49B0.9700
Mn4—N62.2799 (18)C50—H50A0.9600
O1—C11.263 (2)C50—H50B0.9600
O2—C11.252 (2)C50—H50C0.9600
O3—C91.260 (2)C51—C521.509 (3)
O4—C91.258 (2)C51—H51A0.9700
O5—C171.259 (2)C51—H51B0.9700
O6—C171.271 (2)C52—H52A0.9600
O7—C251.257 (3)C52—H52B0.9600
O9—H9A0.94 (3)C52—H52C0.9600
O9—H9B0.937 (18)C53—C541.504 (3)
O11—C43i1.246 (2)C54—C551.383 (3)
O12—C531.258 (2)C54—C591.394 (3)
O13—C531.261 (2)C55—H550.9300
O14—C611.264 (2)C56—C551.382 (3)
O15—C611.248 (2)C56—C571.391 (3)
O16—C691.260 (2)C56—H560.9300
O17—C691.262 (3)C57—C601.505 (3)
O18—C771.256 (2)C58—C591.383 (3)
O19—C771.263 (2)C58—C571.392 (3)
O22—H22A0.92 (3)C58—H580.9300
O22—H22B0.98 (4)C59—H590.9300
N1—C331.338 (3)C60—H60A0.9600
N1—C371.340 (3)C60—H60B0.9600
N2—C381.343 (3)C60—H60C0.9600
N3—C431.338 (3)C62—C611.508 (3)
N3—C441.473 (3)C62—C671.387 (3)
N3—C461.470 (3)C63—C621.392 (3)
N4—C481.327 (3)C63—C641.388 (3)
N4—C491.472 (3)C63—H630.9300
N4—C511.477 (3)C64—H640.9300
N5—C851.338 (3)C65—C661.391 (3)
N5—C891.338 (3)C65—C641.392 (3)
N6—C901.341 (3)C65—C681.509 (3)
N6—C941.337 (3)C66—H660.9300
N7—C951.331 (3)C67—C661.384 (3)
N7—C961.479 (3)C67—H670.9300
N7—C981.470 (3)C68—H68A0.9600
N8—C1001.329 (3)C68—H68B0.9600
N8—C1011.474 (3)C68—H68C0.9600
N8—C1031.472 (2)C70—C691.509 (3)
C1—C21.508 (3)C70—C711.383 (3)
C3—C21.389 (3)C70—C751.391 (3)
C3—H30.9300C71—C721.390 (3)
C4—C31.383 (3)C71—H710.9300
C4—H40.9300C72—C731.382 (3)
C5—C61.390 (3)C72—H720.9300
C5—C41.391 (3)C73—C741.385 (3)
C5—C81.507 (3)C74—H740.9300
C6—C71.387 (3)C75—C741.379 (3)
C6—H60.9300C75—H750.9300
C7—C21.391 (3)C76—C731.514 (3)
C7—H70.9300C76—H76A0.9600
C8—H8A0.9600C76—H76B0.9600
C8—H8B0.9600C76—H76C0.9600
C8—H8C0.9600C77—C781.506 (3)
C9—C101.496 (3)C78—C831.381 (3)
C10—C151.388 (3)C79—C781.384 (3)
C11—C121.386 (3)C79—C801.386 (3)
C11—C101.394 (3)C79—H790.9300
C11—H110.9300C80—H800.9300
C12—C131.388 (3)C81—C801.388 (3)
C12—H120.9300C81—C841.507 (3)
C14—C131.387 (3)C82—C811.389 (3)
C14—C151.388 (3)C82—C831.388 (3)
C14—H140.9300C82—H820.9300
C15—H150.9300C83—H830.9300
C16—C131.505 (3)C84—H84A0.9600
C16—H16A0.9600C84—H84B0.9600
C16—H16B0.9600C84—H84C0.9600
C16—H16C0.9600C85—H850.9300
C18—C171.498 (3)C86—C851.389 (3)
C18—C191.384 (3)C86—C95i1.497 (3)
C18—C231.389 (3)C87—C881.382 (3)
C19—H190.9300C87—C861.395 (3)
C20—C211.385 (3)C87—H870.9300
C20—C191.387 (3)C88—H880.9300
C20—H200.9300C89—C881.376 (3)
C21—C221.391 (3)C89—H890.9300
C21—C241.504 (3)C90—H900.9300
C22—C231.383 (3)C91—C901.380 (3)
C22—H220.9300C91—C921.381 (3)
C23—H230.9300C91—H910.9300
C24—H24A0.9600C92—H920.9300
C24—H24B0.9600C93—C921.389 (3)
C24—H24C0.9600C93—C941.386 (3)
C25—O81.267 (3)C93—C100ii1.502 (3)
C25—C261.506 (3)C94—H940.9300
C26—C271.393 (3)C95—O201.243 (2)
C26—C311.379 (3)C95—C86ii1.497 (3)
C27—H270.9300C96—C971.516 (3)
C28—C271.380 (3)C96—H96A0.9700
C28—H280.9300C96—H96B0.9700
C29—C281.388 (4)C97—H97A0.9600
C29—C301.380 (4)C97—H97B0.9600
C30—H300.9300C97—H97C0.9600
C31—C301.394 (3)C98—C991.517 (3)
C31—H310.9300C98—H98A0.9700
C32—C291.507 (3)C98—H98B0.9700
C32—H32A0.9600C99—H99A0.9600
C32—H32B0.9600C99—H99B0.9600
C32—H32C0.9600C99—H99C0.9600
C33—C341.383 (3)C100—O211.243 (2)
C33—H330.9300C100—C93i1.502 (3)
C34—H340.9300C101—C1021.509 (3)
C35—C341.380 (3)C101—H10A0.9700
C35—C361.387 (3)C101—H10B0.9700
C35—H350.9300C102—H10H0.9600
C36—C48i1.508 (3)C102—H10I0.9600
C37—C361.387 (3)C102—H10J0.9600
C37—H370.9300C103—C1041.512 (3)
C38—H380.9300C103—H10C0.9700
C39—C381.383 (3)C103—H10D0.9700
C39—C401.380 (3)C104—H10E0.9600
C39—H390.9300C104—H10F0.9600
C40—H400.9300C104—H10G0.9600
O2—Mn1—O886.85 (6)N2—C42—H42118.1
O2—Mn1—O992.31 (6)C41—C42—H42118.1
O2—Mn1—O10174.70 (6)O11ii—C43—N3121.49 (19)
O2—Mn1—N284.43 (6)O11ii—C43—C41118.48 (18)
O3—Mn1—O297.60 (6)N3—C43—C41120.00 (18)
O3—Mn1—O8175.43 (6)N3—C44—C45113.85 (19)
O3—Mn1—O991.91 (6)N3—C44—H44A108.8
O3—Mn1—O1086.29 (6)N3—C44—H44B108.8
O3—Mn1—N285.17 (6)C45—C44—H44A108.8
O8—Mn1—O988.92 (6)C45—C44—H44B108.8
O8—Mn1—O1089.21 (6)H44A—C44—H44B107.7
O8—Mn1—N294.29 (6)C44—C45—H45A109.5
O9—Mn1—O1091.16 (6)C44—C45—H45B109.5
O9—Mn1—N2175.29 (6)C44—C45—H45C109.5
O10—Mn1—N292.34 (6)H45A—C45—H45B109.5
O1—Mn2—O6170.61 (6)H45A—C45—H45C109.5
O1—Mn2—O989.49 (6)H45B—C45—H45C109.5
O1—Mn2—O1188.90 (5)N3—C46—C47113.19 (18)
O1—Mn2—N186.27 (6)N3—C46—H46A108.9
O4—Mn2—O197.75 (6)N3—C46—H46B108.9
O4—Mn2—O691.45 (6)C47—C46—H46A108.9
O4—Mn2—O990.02 (6)C47—C46—H46B108.9
O4—Mn2—O1189.10 (5)H46A—C46—H46B107.8
O4—Mn2—N1174.27 (6)C46—C47—H47A109.5
O6—Mn2—O988.61 (5)C46—C47—H47B109.5
O6—Mn2—O1193.15 (5)C46—C47—H47C109.5
O6—Mn2—N184.69 (6)H47A—C47—H47B109.5
O9—Mn2—O11178.04 (6)H47A—C47—H47C109.5
O9—Mn2—N194.11 (6)H47B—C47—H47C109.5
O11—Mn2—N186.89 (6)O10—C48—N4121.96 (19)
O13—Mn3—O17170.86 (6)O10—C48—C36ii119.09 (18)
O13—Mn3—O2184.47 (6)N4—C48—C36ii118.91 (17)
O13—Mn3—O2289.52 (6)N4—C49—C50113.82 (19)
O13—Mn3—N583.28 (6)N4—C49—H49A108.8
O15—Mn3—O13100.63 (6)N4—C49—H49B108.8
O15—Mn3—O1788.49 (6)C50—C49—H49A108.8
O15—Mn3—O21172.45 (6)C50—C49—H49B108.8
O15—Mn3—O2295.02 (6)H49A—C49—H49B107.7
O15—Mn3—N584.32 (6)C49—C50—H50A109.5
O17—Mn3—O2289.03 (6)C49—C50—H50B109.5
O17—Mn3—N598.40 (6)C49—C50—H50C109.5
O21—Mn3—O1786.52 (6)H50A—C50—H50B109.5
O21—Mn3—O2290.55 (6)H50A—C50—H50C109.5
O21—Mn3—N590.82 (6)H50B—C50—H50C109.5
O22—Mn3—N5172.51 (6)N4—C51—C52113.39 (19)
O12—Mn4—O1497.04 (6)N4—C51—H51A108.9
O12—Mn4—O1990.47 (6)N4—C51—H51B108.9
O12—Mn4—O2091.25 (5)C52—C51—H51A108.9
O12—Mn4—O2288.94 (6)C52—C51—H51B108.9
O12—Mn4—N6175.55 (6)H51A—C51—H51B107.7
O14—Mn4—O19172.28 (6)C51—C52—H52A109.5
O14—Mn4—O2089.45 (6)C51—C52—H52B109.5
O14—Mn4—O2292.31 (6)C51—C52—H52C109.5
O14—Mn4—N686.78 (6)H52A—C52—H52B109.5
O19—Mn4—O2088.57 (5)H52A—C52—H52C109.5
O19—Mn4—O2289.64 (6)H52B—C52—H52C109.5
O19—Mn4—N685.65 (6)O12—C53—O13125.68 (19)
O20—Mn4—O22178.20 (6)O12—C53—C54116.39 (18)
O20—Mn4—N686.48 (6)O13—C53—C54117.92 (18)
O22—Mn4—N693.20 (6)C55—C54—C53121.96 (19)
C1—O1—Mn2136.20 (13)C55—C54—C59118.4 (2)
C1—O2—Mn1135.80 (14)C59—C54—C53119.61 (19)
C9—O3—Mn1132.79 (14)C54—C55—H55119.7
C9—O4—Mn2139.38 (13)C56—C55—C54120.7 (2)
C17—O6—Mn2126.66 (13)C56—C55—H55119.7
C25—O8—Mn1126.00 (13)C55—C56—C57121.5 (2)
Mn1—O9—Mn2114.68 (6)C55—C56—H56119.2
Mn1—O9—H9A96.9 (17)C57—C56—H56119.2
Mn1—O9—H9B120 (2)C56—C57—C58117.5 (2)
Mn2—O9—H9A118.6 (17)C56—C57—C60121.4 (2)
Mn2—O9—H9B95 (2)C58—C57—C60121.1 (2)
H9A—O9—H9B113 (3)C57—C58—H58119.4
C48—O10—Mn1139.39 (14)C59—C58—C57121.2 (2)
C43i—O11—Mn2144.18 (14)C59—C58—H58119.4
C53—O12—Mn4138.85 (13)C54—C59—H59119.7
C53—O13—Mn3131.60 (14)C58—C59—C54120.6 (2)
C61—O14—Mn4137.28 (13)C58—C59—H59119.7
C61—O15—Mn3134.89 (14)C57—C60—H60A109.5
C69—O17—Mn3126.80 (13)C57—C60—H60B109.5
C77—O19—Mn4125.56 (13)C57—C60—H60C109.5
C95—O20—Mn4143.45 (14)H60A—C60—H60B109.5
C100—O21—Mn3146.13 (14)H60A—C60—H60C109.5
Mn3—O22—Mn4113.16 (6)H60B—C60—H60C109.5
Mn3—O22—H22A99.9 (16)O14—C61—C62115.51 (18)
Mn3—O22—H22B119 (2)O15—C61—O14126.27 (19)
Mn4—O22—H22A118.4 (16)O15—C61—C62118.21 (18)
Mn4—O22—H22B95 (2)C63—C62—C61121.92 (18)
H22A—O22—H22B113 (3)C67—C62—C61119.52 (18)
C33—N1—Mn2124.49 (14)C67—C62—C63118.56 (19)
C33—N1—C37117.62 (18)C62—C63—H63119.8
C37—N1—Mn2117.75 (14)C64—C63—C62120.5 (2)
C38—N2—Mn1121.24 (14)C64—C63—H63119.8
C42—N2—Mn1120.29 (13)C63—C64—C65121.0 (2)
C42—N2—C38117.38 (18)C63—C64—H64119.5
C43—N3—C44124.34 (18)C65—C64—H64119.5
C43—N3—C46117.55 (17)C64—C65—C68121.5 (2)
C46—N3—C44117.64 (17)C66—C65—C64118.06 (19)
C48—N4—C49119.05 (17)C66—C65—C68120.40 (19)
C48—N4—C51122.86 (18)C65—C66—H66119.5
C49—N4—C51118.08 (17)C67—C66—C65121.0 (2)
C85—N5—Mn3118.94 (13)C67—C66—H66119.5
C85—N5—C89117.71 (18)C62—C67—H67119.6
C89—N5—Mn3122.73 (14)C66—C67—C62120.9 (2)
C90—N6—Mn4126.99 (14)C66—C67—H67119.6
C94—N6—Mn4115.46 (14)C65—C68—H68A109.5
C94—N6—C90117.40 (18)C65—C68—H68B109.5
C95—N7—C96123.95 (18)C65—C68—H68C109.5
C95—N7—C98117.56 (18)H68A—C68—H68B109.5
C98—N7—C96117.96 (17)H68A—C68—H68C109.5
C100—N8—C101118.32 (17)H68B—C68—H68C109.5
C100—N8—C103123.07 (17)O16—C69—O17125.0 (2)
C103—N8—C101118.50 (17)O16—C69—C70116.66 (19)
O1—C1—C2116.18 (18)O17—C69—C70118.28 (19)
O2—C1—O1126.35 (19)C71—C70—C69121.2 (2)
O2—C1—C2117.45 (18)C71—C70—C75118.2 (2)
C3—C2—C1119.81 (19)C75—C70—C69120.65 (19)
C3—C2—C7118.72 (19)C70—C71—C72120.3 (2)
C7—C2—C1121.42 (18)C70—C71—H71119.8
C2—C3—H3119.7C72—C71—H71119.8
C4—C3—C2120.7 (2)C71—C72—H72119.2
C4—C3—H3119.7C73—C72—C71121.7 (2)
C3—C4—C5120.9 (2)C73—C72—H72119.2
C3—C4—H4119.5C72—C73—C74117.5 (2)
C5—C4—H4119.5C72—C73—C76122.1 (2)
C4—C5—C8120.3 (2)C74—C73—C76120.3 (2)
C6—C5—C4118.21 (19)C73—C74—H74119.3
C6—C5—C8121.4 (2)C75—C74—C73121.4 (2)
C5—C6—H6119.5C75—C74—H74119.3
C7—C6—C5121.0 (2)C70—C75—H75119.5
C7—C6—H6119.5C74—C75—C70120.9 (2)
C2—C7—H7119.8C74—C75—H75119.5
C6—C7—C2120.3 (2)C73—C76—H76A109.5
C6—C7—H7119.8C73—C76—H76B109.5
C5—C8—H8A109.5C73—C76—H76C109.5
C5—C8—H8B109.5H76A—C76—H76B109.5
C5—C8—H8C109.5H76A—C76—H76C109.5
H8A—C8—H8B109.5H76B—C76—H76C109.5
H8A—C8—H8C109.5O18—C77—O19125.1 (2)
H8B—C8—H8C109.5O18—C77—C78117.55 (19)
O3—C9—C10117.14 (18)O19—C77—C78117.31 (18)
O4—C9—O3125.93 (19)C83—C78—C79118.6 (2)
O4—C9—C10116.90 (18)C83—C78—C77121.03 (19)
C11—C10—C9120.30 (19)C79—C78—C77120.38 (19)
C15—C10—C9121.41 (19)C78—C79—C80120.6 (2)
C15—C10—C11118.3 (2)C78—C79—H79119.7
C10—C11—H11119.7C80—C79—H79119.7
C12—C11—C10120.5 (2)C79—C80—C81121.4 (2)
C12—C11—H11119.7C79—C80—H80119.3
C11—C12—C13121.1 (2)C81—C80—H80119.3
C11—C12—H12119.4C80—C81—C82117.5 (2)
C13—C12—H12119.4C80—C81—C84121.5 (2)
C12—C13—C16120.8 (2)C82—C81—C84121.0 (2)
C14—C13—C12118.3 (2)C81—C82—H82119.3
C14—C13—C16120.9 (2)C83—C82—C81121.3 (2)
C13—C14—C15120.7 (2)C83—C82—H82119.3
C13—C14—H14119.6C78—C83—C82120.6 (2)
C15—C14—H14119.6C78—C83—H83119.7
C10—C15—C14121.0 (2)C82—C83—H83119.7
C10—C15—H15119.5C81—C84—H84A109.5
C14—C15—H15119.5C81—C84—H84B109.5
C13—C16—H16A109.5C81—C84—H84C109.5
C13—C16—H16B109.5H84A—C84—H84B109.5
C13—C16—H16C109.5H84A—C84—H84C109.5
H16A—C16—H16B109.5H84B—C84—H84C109.5
H16A—C16—H16C109.5N5—C85—C86123.48 (19)
H16B—C16—H16C109.5N5—C85—H85118.3
O5—C17—O6124.73 (19)C86—C85—H85118.3
O5—C17—C18117.28 (18)C85—C86—C87117.8 (2)
O6—C17—C18117.99 (18)C85—C86—C95i117.21 (18)
C19—C18—C17121.26 (19)C87—C86—C95i124.91 (19)
C19—C18—C23118.5 (2)C88—C87—C86118.8 (2)
C23—C18—C17120.26 (19)C88—C87—H87120.6
C18—C19—C20120.7 (2)C86—C87—H87120.6
C18—C19—H19119.6C87—C88—H88120.4
C20—C19—H19119.6C89—C88—C87119.3 (2)
C19—C20—H20119.4C89—C88—H88120.4
C21—C20—C19121.2 (2)N5—C89—C88122.9 (2)
C21—C20—H20119.4N5—C89—H89118.5
C20—C21—C22117.8 (2)C88—C89—H89118.5
C20—C21—C24121.6 (2)N6—C90—C91122.7 (2)
C22—C21—C24120.6 (2)N6—C90—H90118.7
C21—C22—H22119.4C91—C90—H90118.7
C23—C22—C21121.3 (2)C90—C91—C92119.6 (2)
C23—C22—H22119.4C90—C91—H91120.2
C18—C23—H23119.7C92—C91—H91120.2
C22—C23—C18120.5 (2)C91—C92—C93118.3 (2)
C22—C23—H23119.7C91—C92—H92120.8
C21—C24—H24A109.5C93—C92—H92120.8
C21—C24—H24B109.5C92—C93—C100ii124.11 (19)
C21—C24—H24C109.5C94—C93—C92118.32 (19)
H24A—C24—H24B109.5C94—C93—C100ii117.50 (18)
H24A—C24—H24C109.5N6—C94—C93123.62 (19)
H24B—C24—H24C109.5N6—C94—H94118.2
O7—C25—O8125.4 (2)C93—C94—H94118.2
O7—C25—C26116.86 (19)O20—C95—N7121.7 (2)
O8—C25—C26117.77 (19)O20—C95—C86ii118.05 (18)
C31—C26—C27118.6 (2)N7—C95—C86ii120.13 (18)
C31—C26—C25120.8 (2)N7—C96—C97113.40 (19)
C27—C26—C25120.5 (2)N7—C96—H96A108.9
C26—C27—H27119.8N7—C96—H96B108.9
C28—C27—C26120.4 (2)C97—C96—H96A108.9
C28—C27—H27119.8C97—C96—H96B108.9
C27—C28—C29121.5 (3)H96A—C96—H96B107.7
C27—C28—H28119.2C96—C97—H97A109.5
C29—C28—H28119.2C96—C97—H97B109.5
C28—C29—C32120.7 (3)C96—C97—H97C109.5
C30—C29—C28117.6 (2)H97A—C97—H97B109.5
C30—C29—C32121.7 (3)H97A—C97—H97C109.5
C29—C30—C31121.5 (3)H97B—C97—H97C109.5
C29—C30—H30119.3N7—C98—C99113.18 (19)
C31—C30—H30119.3N7—C98—H98A108.9
C26—C31—C30120.3 (2)N7—C98—H98B108.9
C26—C31—H31119.8C99—C98—H98A108.9
C30—C31—H31119.8C99—C98—H98B108.9
C29—C32—H32A109.5H98A—C98—H98B107.8
C29—C32—H32B109.5C98—C99—H99A109.5
C29—C32—H32C109.5C98—C99—H99B109.5
H32A—C32—H32B109.5C98—C99—H99C109.5
H32A—C32—H32C109.5H99A—C99—H99B109.5
H32B—C32—H32C109.5H99A—C99—H99C109.5
N1—C33—C34122.7 (2)H99B—C99—H99C109.5
N1—C33—H33118.7O21—C100—N8121.72 (19)
C34—C33—H33118.7O21—C100—C93i119.68 (18)
C33—C34—H34120.3N8—C100—C93i118.45 (17)
C35—C34—C33119.4 (2)N8—C101—C102112.10 (19)
C35—C34—H34120.3N8—C101—H10A109.2
C34—C35—C36118.6 (2)N8—C101—H10B109.2
C34—C35—H35120.7C102—C101—H10A109.2
C36—C35—H35120.7C102—C101—H10B109.2
C35—C36—C37118.39 (19)H10A—C101—H10B107.9
C35—C36—C48i122.52 (19)C101—C102—H10H109.5
C37—C36—C48i119.01 (18)C101—C102—H10I109.5
N1—C37—C36123.30 (19)C101—C102—H10J109.5
N1—C37—H37118.3H10H—C102—H10I109.5
C36—C37—H37118.3H10H—C102—H10J109.5
N2—C38—C39123.0 (2)H10I—C102—H10J109.5
N2—C38—H38118.5N8—C103—C104113.38 (18)
C39—C38—H38118.5N8—C103—H10C108.9
C38—C39—H39120.5N8—C103—H10D108.9
C40—C39—C38119.0 (2)C104—C103—H10C108.9
C40—C39—H39120.5C104—C103—H10D108.9
C39—C40—C41119.1 (2)H10C—C103—H10D107.7
C39—C40—H40120.5C103—C104—H10E109.5
C41—C40—H40120.5C103—C104—H10F109.5
C40—C41—C43124.26 (19)C103—C104—H10G109.5
C42—C41—C40117.7 (2)H10E—C104—H10F109.5
C42—C41—C43117.84 (18)H10E—C104—H10G109.5
N2—C42—C41123.75 (19)H10F—C104—H10G109.5
O3—Mn1—O2—C179.9 (2)C96—N7—C95—C86ii3.1 (3)
O8—Mn1—O2—C1101.1 (2)C98—N7—C95—O201.9 (3)
O9—Mn1—O2—C112.3 (2)C98—N7—C95—C86ii174.63 (18)
N2—Mn1—O2—C1164.3 (2)C95—N7—C96—C9783.4 (3)
O2—Mn1—O3—C966.64 (18)C98—N7—C96—C9788.1 (2)
O9—Mn1—O3—C925.94 (18)C95—N7—C98—C9972.9 (2)
O10—Mn1—O3—C9116.98 (18)C96—N7—C98—C9999.1 (2)
N2—Mn1—O3—C9150.36 (18)C101—N8—C100—O213.8 (3)
O2—Mn1—O8—C2573.48 (17)C101—N8—C100—C93i171.83 (18)
O9—Mn1—O8—C2518.89 (17)C103—N8—C100—O21179.7 (2)
O10—Mn1—O8—C25110.06 (17)C103—N8—C100—C93i4.2 (3)
N2—Mn1—O8—C25157.65 (17)C100—N8—C101—C10272.1 (2)
O3—Mn1—O9—Mn251.35 (8)C103—N8—C101—C102104.1 (2)
O2—Mn1—O9—Mn246.34 (8)C100—N8—C103—C10498.1 (2)
O8—Mn1—O9—Mn2133.14 (8)C101—N8—C103—C10477.9 (2)
O10—Mn1—O9—Mn2137.67 (7)O1—C1—C2—C311.1 (3)
O3—Mn1—O10—C48152.6 (2)O1—C1—C2—C7166.19 (19)
O8—Mn1—O10—C4826.7 (2)O2—C1—C2—C3170.53 (19)
O9—Mn1—O10—C48115.6 (2)O2—C1—C2—C712.2 (3)
N2—Mn1—O10—C4867.6 (2)C4—C3—C2—C1174.29 (19)
O2—Mn1—N2—C3829.95 (15)C4—C3—C2—C73.1 (3)
O2—Mn1—N2—C42137.82 (15)C5—C4—C3—C20.2 (3)
O3—Mn1—N2—C38128.09 (15)C6—C5—C4—C33.5 (3)
O3—Mn1—N2—C4239.68 (14)C8—C5—C4—C3172.6 (2)
O8—Mn1—N2—C3856.46 (15)C4—C5—C6—C73.4 (3)
O8—Mn1—N2—C42135.77 (14)C8—C5—C6—C7172.6 (2)
O10—Mn1—N2—C38145.84 (15)C5—C6—C7—C20.1 (3)
O10—Mn1—N2—C4246.39 (15)C6—C7—C2—C1174.18 (19)
O4—Mn2—O1—C156.3 (2)C6—C7—C2—C33.1 (3)
O9—Mn2—O1—C133.7 (2)O4—C9—C10—C15169.21 (19)
O11—Mn2—O1—C1145.2 (2)O3—C9—C10—C159.3 (3)
N1—Mn2—O1—C1127.8 (2)O4—C9—C10—C1111.9 (3)
O1—Mn2—O4—C979.6 (2)O3—C9—C10—C11169.58 (19)
O6—Mn2—O4—C998.5 (2)C11—C10—C15—C140.1 (3)
O9—Mn2—O4—C99.9 (2)C9—C10—C15—C14178.75 (19)
O11—Mn2—O4—C9168.3 (2)C12—C11—C10—C150.9 (3)
O4—Mn2—O6—C1779.50 (17)C12—C11—C10—C9177.93 (19)
O9—Mn2—O6—C1710.48 (17)C10—C11—C12—C130.5 (3)
O11—Mn2—O6—C17168.68 (17)C15—C14—C13—C121.5 (3)
N1—Mn2—O6—C17104.74 (17)C15—C14—C13—C16178.7 (2)
O1—Mn2—O9—Mn151.85 (8)C11—C12—C13—C140.7 (3)
O4—Mn2—O9—Mn145.90 (8)C11—C12—C13—C16179.5 (2)
O6—Mn2—O9—Mn1137.35 (8)C13—C14—C15—C101.1 (3)
N1—Mn2—O9—Mn1138.08 (8)C19—C18—C17—O5172.8 (2)
O1—Mn2—N1—C3330.76 (16)C19—C18—C17—O68.2 (3)
O1—Mn2—N1—C37144.83 (14)C23—C18—C17—O56.7 (3)
O6—Mn2—N1—C33146.69 (16)C23—C18—C17—O6172.3 (2)
O6—Mn2—N1—C3737.72 (14)C17—C18—C19—C20179.9 (2)
O9—Mn2—N1—C3358.46 (16)C23—C18—C19—C200.6 (4)
O9—Mn2—N1—C37125.94 (14)C17—C18—C23—C22179.8 (2)
O11—Mn2—N1—C33119.86 (16)C19—C18—C23—C220.3 (3)
O11—Mn2—N1—C3755.74 (14)C21—C20—C19—C180.0 (4)
O15—Mn3—O13—C5366.18 (18)C19—C20—C21—C220.9 (4)
O21—Mn3—O13—C53119.44 (18)C19—C20—C21—C24179.8 (2)
O22—Mn3—O13—C5328.84 (18)C20—C21—C22—C231.1 (4)
N5—Mn3—O13—C53149.08 (18)C24—C21—C22—C23180.0 (2)
O13—Mn3—O15—C6174.1 (2)C21—C22—C23—C180.5 (4)
O17—Mn3—O15—C61105.2 (2)O7—C25—O8—Mn119.4 (3)
O22—Mn3—O15—C6116.3 (2)C26—C25—O8—Mn1160.32 (13)
N5—Mn3—O15—C61156.2 (2)O7—C25—C26—C275.1 (3)
O15—Mn3—O17—C6983.06 (17)O7—C25—C26—C31171.9 (2)
O21—Mn3—O17—C69102.60 (17)O8—C25—C26—C27175.1 (2)
O22—Mn3—O17—C6911.99 (17)O8—C25—C26—C317.9 (3)
N5—Mn3—O17—C69167.09 (17)C31—C26—C27—C280.5 (3)
O13—Mn3—O21—C100156.8 (3)C25—C26—C27—C28177.6 (2)
O17—Mn3—O21—C10024.7 (3)C25—C26—C31—C30176.5 (2)
O22—Mn3—O21—C100113.7 (3)C27—C26—C31—C300.6 (3)
N5—Mn3—O21—C10073.6 (3)C29—C28—C27—C261.3 (4)
O13—Mn3—O22—Mn456.91 (8)C30—C29—C28—C271.1 (4)
O15—Mn3—O22—Mn443.72 (8)C32—C29—C28—C27178.4 (2)
O17—Mn3—O22—Mn4132.11 (8)C28—C29—C30—C310.0 (4)
O21—Mn3—O22—Mn4141.38 (8)C32—C29—C30—C31179.5 (2)
O13—Mn3—N5—C8544.99 (14)C26—C31—C30—C290.8 (4)
O13—Mn3—N5—C89125.77 (16)N1—C33—C34—C350.8 (3)
O15—Mn3—N5—C85146.43 (14)C36—C35—C34—C331.5 (3)
O15—Mn3—N5—C8924.33 (15)C34—C35—C36—C370.8 (3)
O17—Mn3—N5—C85125.95 (14)C34—C35—C36—C48i177.45 (18)
O17—Mn3—N5—C8963.30 (16)N1—C37—C36—C350.8 (3)
O21—Mn3—N5—C8539.35 (14)N1—C37—C36—C48i175.99 (18)
O21—Mn3—N5—C89149.90 (15)C40—C39—C38—N20.0 (3)
O14—Mn4—O12—C5384.7 (2)C38—C39—C40—C411.6 (3)
O19—Mn4—O12—C5397.1 (2)C42—C41—C40—C391.5 (3)
O20—Mn4—O12—C53174.3 (2)C43—C41—C40—C39173.70 (18)
O22—Mn4—O12—C537.5 (2)C40—C41—C42—N20.2 (3)
O12—Mn4—O14—C6159.5 (2)C43—C41—C42—N2175.73 (17)
O20—Mn4—O14—C61150.7 (2)C40—C41—C43—O11ii120.2 (2)
O22—Mn4—O14—C6129.7 (2)C40—C41—C43—N361.7 (3)
N6—Mn4—O14—C61122.8 (2)C42—C41—C43—O11ii55.0 (3)
O12—Mn4—O19—C7766.94 (17)C42—C41—C43—N3123.1 (2)
O20—Mn4—O19—C77158.19 (17)C41—C42—N2—Mn1166.44 (15)
O22—Mn4—O19—C7722.00 (17)C41—C42—N2—C381.8 (3)
N6—Mn4—O19—C77115.24 (17)N4—C48—O10—Mn1132.5 (2)
O12—Mn4—O20—C9586.5 (2)C36ii—C48—O10—Mn149.8 (3)
O14—Mn4—O20—C9510.5 (2)O12—C53—C54—C55167.60 (19)
O19—Mn4—O20—C95177.0 (2)O12—C53—C54—C5911.5 (3)
N6—Mn4—O20—C9597.3 (2)O13—C53—C54—C5510.8 (3)
O12—Mn4—O22—Mn350.24 (8)O13—C53—C54—C59170.05 (19)
O14—Mn4—O22—Mn346.76 (8)C53—C54—C55—C56177.29 (19)
O19—Mn4—O22—Mn3140.72 (8)C59—C54—C55—C561.8 (3)
N6—Mn4—O22—Mn3133.66 (8)C55—C54—C59—C581.1 (3)
O14—Mn4—N6—C9037.95 (16)C53—C54—C59—C58178.02 (19)
O14—Mn4—N6—C94137.43 (14)C57—C56—C55—C540.9 (3)
O19—Mn4—N6—C90143.58 (17)C55—C56—C57—C580.8 (3)
O19—Mn4—N6—C9441.05 (14)C55—C56—C57—C60178.4 (2)
O20—Mn4—N6—C90127.59 (17)C59—C58—C57—C561.6 (3)
O20—Mn4—N6—C9447.78 (14)C59—C58—C57—C60177.7 (2)
O22—Mn4—N6—C9054.18 (17)C57—C58—C59—C540.6 (3)
O22—Mn4—N6—C94130.44 (14)C67—C62—C61—O1412.2 (3)
Mn2—O1—C1—O21.6 (4)C67—C62—C61—O15168.26 (19)
Mn2—O1—C1—C2176.61 (13)C63—C62—C61—O14168.89 (19)
Mn1—O2—C1—O112.9 (3)C63—C62—C61—O1510.7 (3)
Mn1—O2—C1—C2168.92 (14)C61—C62—C67—C66179.78 (19)
Mn1—O3—C9—O49.7 (3)C63—C62—C67—C661.3 (3)
Mn1—O3—C9—C10172.00 (13)C64—C63—C62—C61179.99 (19)
Mn2—O4—C9—O321.0 (3)C64—C63—C62—C671.1 (3)
Mn2—O4—C9—C10160.69 (15)C62—C63—C64—C650.0 (3)
Mn2—O6—C17—O53.8 (3)C66—C65—C64—C630.8 (3)
Mn2—O6—C17—C18175.16 (13)C68—C65—C64—C63177.7 (2)
C43i—O11—Mn2—O10.3 (2)C64—C65—C66—C670.6 (3)
C43i—O11—Mn2—O498.0 (2)C68—C65—C66—C67177.9 (2)
C43i—O11—Mn2—O6170.5 (2)C62—C67—C66—C650.4 (3)
C43i—O11—Mn2—N186.0 (2)C71—C70—C69—O16175.77 (19)
Mn4—O12—C53—O1327.6 (3)C71—C70—C69—O175.0 (3)
Mn4—O12—C53—C54154.13 (16)C75—C70—C69—O166.0 (3)
Mn3—O13—C53—O1212.3 (3)C75—C70—C69—O17173.2 (2)
Mn3—O13—C53—C54169.43 (13)C69—C70—C71—C72177.3 (2)
Mn4—O14—C61—O151.2 (4)C75—C70—C71—C720.9 (3)
Mn4—O14—C61—C62178.30 (14)C69—C70—C75—C74176.7 (2)
Mn3—O15—C61—O147.7 (3)C71—C70—C75—C741.6 (3)
Mn3—O15—C61—C62172.76 (13)C70—C71—C72—C731.2 (3)
Mn3—O17—C69—O168.6 (3)C71—C72—C73—C742.7 (3)
Mn3—O17—C69—C70170.54 (13)C71—C72—C73—C76175.6 (2)
Mn4—O19—C77—O1810.9 (3)C72—C73—C74—C752.0 (4)
Mn4—O19—C77—C78169.13 (14)C76—C73—C74—C75176.3 (2)
Mn2—N1—C33—C34174.91 (15)C70—C75—C74—C730.1 (4)
C37—N1—C33—C340.7 (3)O18—C77—C78—C791.4 (3)
Mn2—N1—C37—C36174.37 (15)O18—C77—C78—C83178.0 (2)
C33—N1—C37—C361.5 (3)O19—C77—C78—C79178.6 (2)
Mn1—N2—C38—C39166.40 (15)O19—C77—C78—C832.0 (3)
C42—N2—C38—C391.7 (3)C77—C78—C83—C82179.8 (2)
C44—N3—C43—O11ii170.87 (19)C79—C78—C83—C820.4 (4)
C44—N3—C43—C417.1 (3)C80—C79—C78—C77179.9 (2)
C46—N3—C43—O11ii1.0 (3)C80—C79—C78—C830.7 (3)
C46—N3—C43—C41178.99 (18)C78—C79—C80—C810.9 (4)
C43—N3—C44—C4589.3 (3)C82—C81—C80—C790.9 (4)
C46—N3—C44—C4582.6 (2)C84—C81—C80—C79180.0 (2)
C43—N3—C46—C4772.9 (2)C83—C82—C81—C800.6 (4)
C44—N3—C46—C4799.5 (2)C83—C82—C81—C84179.8 (2)
C49—N4—C48—O100.3 (3)C81—C82—C83—C780.4 (4)
C49—N4—C48—C36ii178.03 (18)C87—C86—C85—N51.1 (3)
C51—N4—C48—O10178.5 (2)C95i—C86—C85—N5177.86 (17)
C51—N4—C48—C36ii0.8 (3)C88—C87—C86—C850.2 (3)
C48—N4—C49—C5077.2 (3)C88—C87—C86—C95i176.26 (18)
C51—N4—C49—C50101.6 (2)N5—C89—C88—C870.9 (3)
C48—N4—C51—C5297.0 (3)C86—C87—C88—C891.1 (3)
C49—N4—C51—C5281.8 (2)C92—C91—C90—N61.1 (3)
Mn3—N5—C85—C86169.80 (15)C90—C91—C92—C932.6 (3)
Mn3—N5—C89—C88170.47 (15)C94—C93—C92—C912.0 (3)
C85—N5—C89—C880.4 (3)C100ii—C93—C92—C91178.93 (19)
C89—N5—C85—C861.4 (3)C92—C93—C94—N60.3 (3)
Mn4—N6—C90—C91174.16 (15)C100ii—C93—C94—N6176.89 (18)
Mn4—N6—C94—C93174.02 (15)N7—C95—O20—Mn4100.6 (3)
C94—N6—C90—C911.1 (3)C86ii—C95—O20—Mn482.8 (3)
C90—N6—C94—C931.8 (3)N8—C100—O21—Mn3134.9 (2)
C96—N7—C95—O20173.37 (19)C93i—C100—O21—Mn349.5 (3)
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg5, Cg10 and Cg12 are the centroids of the C2–C7, N1/C33–C37, C78–C83 and N6/C90–C94 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O9—H9A···O70.94 (3)1.62 (3)2.552 (2)170 (3)
O9—H9B···O50.94 (2)1.59 (2)2.520 (2)173 (3)
O22—H22A···O160.92 (3)1.64 (3)2.544 (2)166 (2)
O22—H22B···O180.97 (4)1.60 (4)2.558 (2)169 (3)
C52—H52A···Cg12ii0.962.873.782 (3)160
C60—H60C···Cg1iii0.962.993.841 (3)149
C84—H84B···Cg10iv0.962.883.609 (3)134
C104—H10E···Cg5i0.962.823.709 (3)155
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x, y, z+1; (iv) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula[Mn2(C8H7O2)4(C10H14N2O)2(H2O)]
Mr1024.90
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)10.5228 (2), 19.1361 (3), 26.6008 (4)
α, β, γ (°)70.537 (2), 78.836 (3), 88.485 (3)
V3)4950.63 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.57
Crystal size (mm)0.35 × 0.24 × 0.15
Data collection
DiffractometerBruker Kappa APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.848, 0.917
No. of measured, independent and
observed [I > 2σ(I)] reflections
87669, 24563, 17121
Rint0.049
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.102, 1.02
No. of reflections24563
No. of parameters1275
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.51

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg5, Cg10 and Cg12 are the centroids of the C2–C7, N1/C33–C37, C78–C83 and N6/C90–C94 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O9—H9A···O70.94 (3)1.62 (3)2.552 (2)170 (3)
O9—H9B···O50.94 (2)1.59 (2)2.520 (2)173 (3)
O22—H22A···O160.92 (3)1.64 (3)2.544 (2)166 (2)
O22—H22B···O180.97 (4)1.60 (4)2.558 (2)169 (3)
C52—H52A···Cg12i0.962.873.782 (3)160
C60—H60C···Cg1ii0.962.993.841 (3)149
C84—H84B···Cg10iii0.962.883.609 (3)134
C104—H10E···Cg5iv0.962.823.709 (3)155
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) x+1, y, z+1; (iv) x1, y, z.
 

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University for the use of the diffractometer. This work was supported financially by Kafkas University Research Fund (grant No. 2009-FEF-03).

References

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Volume 66| Part 7| July 2010| Pages m734-m735
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