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Acta Cryst. (2011). E67, m1128-m1129    [ doi:10.1107/S1600536811028492 ]

Di-[mu]-nicotinamide-[kappa]2N1:O;[kappa]2O:N1-bis[aquabis(4-bromobenzoato)-[kappa]O;[kappa]2O,O'-manganese(II)]

H. Necefoglu, F. E. Özbek, V. Öztürk, V. Adigüzel and T. Hökelek

Abstract top

In the centrosymmetric dinuclear title compound, [Mn2(C7H4BrO2)4(C6H6N2O)2(H2O)2], the MnII atom is coordinated by one N atom from one bridging nicotinamide ligand and one O atom from another symmetry-related bridging nicotinamide ligand, three O atoms from two 4-bromobenzoate ligands and one water molecule in a distorted octahedral geometry. The dihedral angles between the carboxylate groups and the adjacent benzene rings are 10.89 (16) and 8.4 (2)°, while the benzene rings are oriented at a dihedral angle of 6.09 (13)°. Intermolecular O-H...O, N-H...O and weak C-H...O hydrogen bonds link the molecules into a three-dimensional network. [pi]-[pi] interactions, indicated by short centroid-centroid distances [3.845 (2) Å between the benzene rings, 3.650 (2) Å between the pyridine rings and 3.700 (3) Å between the benzene and pyridine rings] further stabilize the structure.

Comment top

As a part of our ongoing investigations of transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

The title compound, (I), consists of dimeric units located around a crystallographic symmetry centre and made up of two Mn cations, four 4-bromobenzoate (PBB) anions, which act in different modes-monodentate, bidentate and bidentate, monodentate, respectively, two nicotinamide (NA) ligands and two water molecules (Fig. 1). Both of the MnII centres are six-coordinated, and the two monomeric units are bridged through the two nicotinamide (NA) ligands about an inversion center. The Mn1···Mn1i [symmetry code: (i) -x, -y, -z] distance is 7.180 (2) Å. In the molecule, one Mn—O bond distance [2.316 (2) Å] is significantly longer than the other four, and the average Mn—O bond length is 2.193 (2) Å (Table 1). The Mn atom is displaced out of the least-squares planes of the carboxylate groups (O1/C1/O2) and (O3/C8/O4) by -0.0925 (5) and -0.5744 (5) Å, respectively.

The dihedral angles between the planar carboxylate groups and the adjacent benzene rings A (C2—C7) and B (C9—C14) are 10.89 (16) and 8.37 (20) °, respectively, while those between rings A, B and C (N1/C15—C19) are A/B = 6.09 (13), A/C = 85.37 (11), B/C = 86.41 (13) °.

In (I), the O1-Mn1-O2 angle is 57.61 (8)°. The corresponding O—M—O (where M is a metal) angles are 57.75 (2)° in [Cu(C7H5O2F)(C7H4O2F)2(C6H6N2O)2], (II) (Necefoğlu et al., 2011), 60.32 (4)° in [Co(C8H7O3)2(C6H6N2O)(H2O)2], (III) (Hökelek et al., 2010a), 59.02 (8)° in [Zn(C8H8NO2)2(C6H6N2O)2].H2O, (IV) (Hökelek et al., 2009a), 60.03 (6)° in [Zn(C9H10NO2)2(C6H6N2O)2(H2O)2], (V) (Hökelek et al., 2009b), 57.53 (5)°, 56.19 (5)° and 59.04 (4)° in [Zn(C8H7O3)2(C6H6N2O)2], (VI) (Hökelek et al., 2010b) and 55.2 (1)° in [Cu(Asp)2(py)2] (where Asp is acetylsalicylate and py is pyridine) [(VII); Greenaway et al., 1984].

In the crystal structure, intermolecular O—H···O, N—H···O and C—H···O hydrogen bonds link the molecules into a three dimensional network (Table 2, Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contacts between the benzene rings, between the pyridine rings and the benzene and pyridine rings Cg1—Cg1i, Cg3—Cg3ii and Cg1—Cg2iii [symmetry codes: (i) 2 - x, -y, -z; (ii) 3 - x, 1 - y, 1 - z; (iii) 2 - x, -y, 1 - z, where Cg1, Cg2 and Cg3 are the centroids of the rings A (C2—C7), B (C9—C14) and C (N1/C15—C19), respectively] may further stabilize the structure, with centroid-centroid distances of 3.845 (2), 3.650 (2) and 3.700 (3) Å, respectively.

Related literature top

For niacin, see: Krishnamachari (1974). For information on the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Hökelek et al. (2009a,b); Hökelek et al. (2010a,b); Necefoğlu et al. (2011); Greenaway et al. (1984).

Experimental top

The title compound was prepared by the reaction of MnSO4.H2O (0.85 g, 10 mmol) in H2O (25 ml) and nicotinamide (1.22 g, 20 mmol) in H2O (25 ml) with sodium 4-bromobenzoate (2.23 g, 20 mmol) in H2O (100 ml) at room temperature. The mixture was filtered and set aside to crystallize at ambient temperature for a few days, giving colorless single crystals.

Refinement top

Atoms H6A, H6B (for H2O) and H2A, H2B (for NH2) were located in a difference Fourier map and were freely refined. The C-bound H-atoms were positioned geometrically with C—H = 0.93 Å for aromatic H-atoms, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

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: ORTEP-3 for Windows (Farrugia, 1997); 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 50% probability level [symmetry code: (') -x, -y, -z].
[Figure 2] Fig. 2. A view of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines. [H-atoms not involved in hydrogen bonding have been omitted for clarity].
Di-µ-nicotinamide-κ2N1:O;κ2O:N1- bis[aquabis(4-bromobenzoato)-κO;κ2O,O'-manganese(II)] top
Crystal data top
[Mn2(C7H4BrO2)4(C6H6N2O)2(H2O)2]Z = 1
Mr = 1190.18F(000) = 586
Triclinic, P1Dx = 1.836 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2213 (2) ÅCell parameters from 7870 reflections
b = 12.1782 (3) Åθ = 2.9–28.1°
c = 13.4931 (4) ŵ = 4.37 mm−1
α = 110.038 (3)°T = 294 K
β = 91.206 (2)°Block, colorless
γ = 103.653 (2)°0.29 × 0.22 × 0.20 mm
V = 1076.51 (6) Å3
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer		5394 independent reflections
Radiation source: fine-focus sealed tube4298 reflections with I > 2σ(I)
graphiteRint = 0.039
φ and ω scansθmax = 28.6°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −9→9
Tmin = 0.329, Tmax = 0.418k = −16→16
18469 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)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0463P)2 + 2.4514P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
5394 reflectionsΔρmax = 2.03 e Å−3
297 parametersΔρmin = −1.76 e Å−3
4 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0235 (13)
Crystal data top
[Mn2(C7H4BrO2)4(C6H6N2O)2(H2O)2]γ = 103.653 (2)°
Mr = 1190.18V = 1076.51 (6) Å3
Triclinic, P1Z = 1
a = 7.2213 (2) ÅMo Kα radiation
b = 12.1782 (3) ŵ = 4.37 mm−1
c = 13.4931 (4) ÅT = 294 K
α = 110.038 (3)°0.29 × 0.22 × 0.20 mm
β = 91.206 (2)°
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer		5394 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		4298 reflections with I > 2σ(I)
Tmin = 0.329, Tmax = 0.418Rint = 0.039
18469 measured reflectionsθmax = 28.6°
Refinement top
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126Δρmax = 2.03 e Å−3
S = 1.05Δρmin = −1.76 e Å−3
5394 reflectionsAbsolute structure: ?
297 parametersFlack parameter: ?
4 restraintsRogers parameter: ?
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 > 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
Mn10.03281 (7)0.20681 (4)0.48986 (4)0.02469 (14)
Br10.08035 (10)−0.25888 (5)−0.16236 (4)0.0704 (2)
Br2−0.35117 (11)0.46846 (7)1.09799 (4)0.0875 (3)
O1−0.0971 (3)0.0349 (2)0.34227 (19)0.0305 (5)
O20.1724 (3)0.1626 (2)0.33974 (19)0.0294 (5)
O3−0.1656 (5)0.1988 (3)0.5927 (3)0.0537 (8)
O4−0.3453 (4)0.0368 (2)0.6157 (2)0.0470 (7)
O5−0.1222 (3)0.3095 (2)0.4261 (2)0.0320 (5)
O60.2150 (4)0.1154 (2)0.5439 (2)0.0326 (5)
H6A0.174 (7)0.083 (5)0.588 (3)0.068 (17)*
H6B0.259 (6)0.066 (3)0.496 (3)0.042 (12)*
N10.2516 (4)0.3847 (2)0.5796 (2)0.0291 (6)
N2−0.4244 (4)0.1935 (3)0.3759 (3)0.0369 (7)
H2A−0.541 (3)0.187 (4)0.357 (4)0.054 (14)*
H2B−0.394 (7)0.133 (3)0.384 (4)0.053 (13)*
C10.0442 (4)0.0650 (3)0.2952 (2)0.0243 (6)
C20.0602 (5)−0.0145 (3)0.1855 (3)0.0281 (7)
C3−0.0629 (5)−0.1295 (3)0.1423 (3)0.0358 (8)
H3−0.1523−0.15710.18270.043*
C4−0.0537 (6)−0.2035 (4)0.0392 (3)0.0439 (9)
H4−0.1349−0.28110.01060.053*
C50.0761 (6)−0.1610 (4)−0.0197 (3)0.0433 (9)
C60.2021 (6)−0.0479 (4)0.0219 (3)0.0453 (9)
H60.2915−0.0212−0.01900.054*
C70.1942 (5)0.0256 (3)0.1250 (3)0.0354 (8)
H70.27890.10210.15380.043*
C8−0.2679 (5)0.1464 (3)0.6458 (3)0.0318 (7)
C9−0.2941 (5)0.2254 (3)0.7544 (3)0.0314 (7)
C10−0.1872 (6)0.3452 (3)0.7977 (3)0.0412 (9)
H10−0.10260.37690.75740.049*
C11−0.2037 (7)0.4181 (4)0.8993 (4)0.0515 (11)
H11−0.13320.49860.92730.062*
C12−0.3271 (7)0.3688 (4)0.9580 (3)0.0512 (11)
C13−0.4343 (6)0.2518 (5)0.9188 (4)0.0522 (11)
H13−0.51710.22070.96020.063*
C14−0.4181 (6)0.1794 (4)0.8158 (3)0.0425 (9)
H14−0.49110.09950.78810.051*
C150.2168 (5)0.4876 (3)0.5798 (3)0.0291 (7)
H150.09450.48450.55390.035*
C160.3514 (4)0.5991 (3)0.6163 (2)0.0235 (6)
C170.5302 (5)0.6036 (3)0.6579 (3)0.0313 (7)
H170.62490.67620.68340.038*
C180.5661 (5)0.4984 (3)0.6609 (3)0.0373 (8)
H180.68520.49980.68970.045*
C190.4250 (5)0.3911 (3)0.6212 (3)0.0325 (7)
H190.45150.32080.62340.039*
C20−0.2925 (4)0.2957 (3)0.3966 (3)0.0252 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0273 (2)0.0187 (2)0.0281 (3)0.00505 (17)0.00231 (18)0.00905 (18)
Br10.1104 (5)0.0750 (4)0.0318 (2)0.0543 (3)0.0100 (2)0.0063 (2)
Br20.1231 (6)0.1180 (5)0.0361 (3)0.0877 (5)0.0081 (3)0.0083 (3)
O10.0304 (12)0.0269 (11)0.0325 (12)0.0038 (9)0.0061 (10)0.0109 (9)
O20.0269 (11)0.0266 (11)0.0337 (12)0.0043 (9)0.0009 (9)0.0114 (9)
O30.0640 (19)0.0517 (17)0.0500 (18)0.0148 (15)0.0300 (15)0.0226 (14)
O40.0580 (18)0.0320 (13)0.0502 (17)0.0133 (12)0.0130 (14)0.0123 (12)
O50.0243 (11)0.0230 (10)0.0482 (15)0.0044 (9)−0.0054 (10)0.0138 (10)
O60.0429 (14)0.0239 (11)0.0354 (14)0.0116 (10)0.0044 (11)0.0141 (10)
N10.0297 (14)0.0208 (12)0.0361 (15)0.0041 (10)−0.0034 (11)0.0113 (11)
N20.0276 (15)0.0221 (13)0.060 (2)0.0016 (11)−0.0041 (14)0.0175 (14)
C10.0263 (15)0.0230 (13)0.0264 (15)0.0076 (11)−0.0012 (12)0.0116 (12)
C20.0300 (16)0.0301 (15)0.0274 (16)0.0121 (13)0.0007 (13)0.0117 (13)
C30.0403 (19)0.0303 (16)0.0323 (18)0.0080 (14)0.0012 (15)0.0065 (14)
C40.054 (2)0.0332 (18)0.038 (2)0.0134 (17)−0.0039 (17)0.0047 (16)
C50.060 (2)0.047 (2)0.0288 (18)0.034 (2)0.0022 (17)0.0079 (16)
C60.050 (2)0.060 (3)0.039 (2)0.027 (2)0.0165 (18)0.0250 (19)
C70.0354 (18)0.0396 (18)0.0342 (19)0.0113 (15)0.0048 (14)0.0157 (15)
C80.0300 (16)0.0357 (17)0.0366 (18)0.0163 (14)0.0073 (14)0.0161 (14)
C90.0319 (17)0.0359 (17)0.0351 (18)0.0183 (14)0.0065 (14)0.0171 (14)
C100.049 (2)0.0363 (19)0.042 (2)0.0151 (16)0.0051 (17)0.0163 (16)
C110.070 (3)0.040 (2)0.044 (2)0.025 (2)−0.003 (2)0.0081 (18)
C120.064 (3)0.064 (3)0.033 (2)0.046 (2)0.0022 (19)0.0071 (19)
C130.045 (2)0.079 (3)0.047 (2)0.031 (2)0.0176 (19)0.030 (2)
C140.038 (2)0.050 (2)0.045 (2)0.0143 (17)0.0127 (17)0.0219 (18)
C150.0259 (15)0.0221 (14)0.0378 (18)0.0033 (12)−0.0062 (13)0.0112 (13)
C160.0248 (14)0.0196 (13)0.0263 (15)0.0047 (11)0.0018 (11)0.0092 (11)
C170.0259 (15)0.0255 (15)0.0408 (19)0.0019 (12)−0.0053 (13)0.0134 (14)
C180.0289 (17)0.0336 (17)0.051 (2)0.0064 (14)−0.0079 (15)0.0190 (16)
C190.0361 (18)0.0255 (15)0.0391 (19)0.0096 (13)−0.0021 (14)0.0148 (14)
C200.0262 (15)0.0196 (13)0.0278 (15)0.0053 (11)0.0008 (12)0.0064 (11)
Geometric parameters (Å, °) top
Mn1—O12.316 (2)C6—C51.377 (6)
Mn1—O22.237 (2)C6—H60.9300
Mn1—O32.025 (3)C7—C61.384 (6)
Mn1—C12.619 (3)C7—H70.9300
Br1—C51.891 (4)C9—C81.497 (5)
Br2—C121.901 (4)C9—C101.389 (5)
O1—C11.260 (4)C9—C141.384 (5)
O2—C11.265 (4)C10—C111.380 (6)
O3—C81.257 (4)C10—H100.9300
O4—C81.235 (4)C11—H110.9300
Mn1—O52.217 (2)C12—C131.362 (7)
O5—C201.239 (4)C12—C111.373 (7)
Mn1—O62.170 (2)C13—H130.9300
O6—H6A0.845 (19)C14—C131.392 (6)
O6—H6B0.847 (19)C14—H140.9300
Mn1—N12.272 (3)C15—C161.389 (4)
N1—C151.334 (4)C15—H150.9300
N1—C191.335 (4)C16—C171.378 (4)
N2—H2A0.853 (19)C16—C20i1.503 (4)
N2—H2B0.857 (19)C17—H170.9300
C1—C21.490 (5)C18—C171.380 (5)
C2—C31.386 (5)C18—H180.9300
C2—C71.388 (5)C19—C181.379 (5)
C3—C41.388 (5)C19—H190.9300
C3—H30.9300C20—N21.314 (4)
C4—H40.9300C20—C16i1.503 (4)
C5—C41.364 (6)
O1—Mn1—C128.77 (9)C4—C5—Br1119.1 (3)
O2—Mn1—O157.61 (8)C4—C5—C6121.6 (4)
O2—Mn1—N196.47 (10)C6—C5—Br1119.3 (3)
O2—Mn1—C128.85 (9)C5—C6—C7119.3 (4)
O3—Mn1—O1102.93 (11)C5—C6—H6120.3
O3—Mn1—O2160.32 (12)C7—C6—H6120.3
O3—Mn1—O589.12 (12)C2—C7—H7120.0
O3—Mn1—O697.50 (12)C6—C7—C2120.1 (4)
O3—Mn1—N1102.86 (12)C6—C7—H7120.0
O3—Mn1—C1131.68 (12)O3—C8—C9116.0 (3)
O5—Mn1—O189.54 (9)O4—C8—O3125.3 (4)
O5—Mn1—O287.89 (9)O4—C8—C9118.7 (3)
O5—Mn1—N187.93 (9)C10—C9—C8120.6 (3)
O5—Mn1—C189.17 (9)C14—C9—C8120.8 (3)
O6—Mn1—O191.37 (9)C14—C9—C10118.5 (4)
O6—Mn1—O286.68 (9)C9—C10—H10119.3
O6—Mn1—O5172.93 (10)C11—C10—C9121.4 (4)
O6—Mn1—N188.18 (10)C11—C10—H10119.3
O6—Mn1—C188.26 (10)C10—C11—H11120.9
N1—Mn1—O1154.04 (10)C12—C11—C10118.2 (4)
N1—Mn1—C1125.32 (10)C12—C11—H11120.9
C1—O1—Mn189.05 (18)C11—C12—Br2118.6 (4)
C1—O2—Mn192.58 (19)C13—C12—Br2119.1 (4)
C8—O3—Mn1152.3 (3)C13—C12—C11122.3 (4)
C20—O5—Mn1134.3 (2)C12—C13—C14119.0 (4)
Mn1—O6—H6B116 (3)C12—C13—H13120.5
Mn1—O6—H6A117 (4)C14—C13—H13120.5
H6B—O6—H6A108 (5)C9—C14—C13120.5 (4)
C15—N1—Mn1118.9 (2)C9—C14—H14119.7
C15—N1—C19117.4 (3)C13—C14—H14119.7
C19—N1—Mn1123.1 (2)N1—C15—C16124.2 (3)
C20—N2—H2A121 (3)N1—C15—H15117.9
C20—N2—H2B120 (3)C16—C15—H15117.9
H2A—N2—H2B119 (5)C15—C16—C20i117.2 (3)
O1—C1—Mn162.18 (17)C17—C16—C15117.5 (3)
O1—C1—O2120.7 (3)C17—C16—C20i125.2 (3)
O1—C1—C2119.9 (3)C16—C17—C18118.8 (3)
O2—C1—Mn158.57 (17)C16—C17—H17120.6
O2—C1—C2119.4 (3)C18—C17—H17120.6
C2—C1—Mn1177.4 (2)C17—C18—H18120.1
C3—C2—C1119.6 (3)C19—C18—C17119.9 (3)
C3—C2—C7119.4 (3)C19—C18—H18120.1
C7—C2—C1121.0 (3)N1—C19—C18122.2 (3)
C2—C3—C4120.4 (4)N1—C19—H19118.9
C2—C3—H3119.8C18—C19—H19118.9
C4—C3—H3119.8O5—C20—N2123.2 (3)
C3—C4—H4120.4O5—C20—C16i118.5 (3)
C5—C4—C3119.1 (4)N2—C20—C16i118.3 (3)
C5—C4—H4120.4
O2—Mn1—O1—C11.32 (17)C19—N1—Mn1—O1−78.8 (4)
O3—Mn1—O1—C1178.1 (2)C19—N1—Mn1—O2−75.9 (3)
O3—Mn1—O2—C1−10.6 (4)C19—N1—Mn1—O3107.9 (3)
O5—Mn1—O1—C189.11 (19)C19—N1—Mn1—O5−163.5 (3)
O6—Mn1—O1—C1−83.88 (19)C19—N1—Mn1—O610.6 (3)
N1—Mn1—O1—C14.8 (3)C19—N1—Mn1—C1−76.0 (3)
O1—Mn1—O2—C1−1.31 (17)Mn1—N1—C15—C16−168.9 (3)
O5—Mn1—O2—C1−92.11 (18)C19—N1—C15—C162.8 (5)
O6—Mn1—O2—C192.42 (18)Mn1—N1—C19—C18169.8 (3)
N1—Mn1—O2—C1−179.79 (18)C15—N1—C19—C18−1.5 (6)
O1—Mn1—O3—C856.2 (7)O1—C1—C2—C3−10.1 (5)
O2—Mn1—O3—C864.3 (8)O2—C1—C2—C3170.3 (3)
O5—Mn1—O3—C8145.5 (7)O1—C1—C2—C7168.6 (3)
O6—Mn1—O3—C8−37.0 (7)O2—C1—C2—C7−10.9 (5)
N1—Mn1—O3—C8−126.8 (6)C1—C2—C3—C4178.2 (3)
C1—Mn1—O3—C857.4 (7)C7—C2—C3—C4−0.6 (5)
O1—Mn1—C1—O2177.7 (3)C1—C2—C7—C6−177.6 (3)
O2—Mn1—C1—O1−177.7 (3)C3—C2—C7—C61.2 (5)
O3—Mn1—C1—O1−2.5 (3)C2—C3—C4—C5−1.0 (6)
O3—Mn1—C1—O2175.22 (19)Br1—C5—C4—C3−177.0 (3)
O5—Mn1—C1—O1−90.56 (18)C6—C5—C4—C32.0 (6)
O5—Mn1—C1—O287.14 (18)C7—C6—C5—Br1177.6 (3)
O6—Mn1—C1—O196.03 (19)C7—C6—C5—C4−1.5 (6)
O6—Mn1—C1—O2−86.28 (18)C2—C7—C6—C5−0.2 (6)
N1—Mn1—C1—O1−177.43 (17)C10—C9—C8—O3−9.3 (5)
N1—Mn1—C1—O20.3 (2)C10—C9—C8—O4170.2 (3)
Mn1—O1—C1—O2−2.3 (3)C14—C9—C8—O3173.9 (4)
Mn1—O1—C1—C2178.2 (3)C14—C9—C8—O4−6.5 (5)
Mn1—O2—C1—O12.4 (3)C8—C9—C10—C11−177.4 (4)
Mn1—O2—C1—C2−178.1 (2)C14—C9—C10—C11−0.6 (6)
Mn1—O3—C8—O4−37.6 (9)C8—C9—C14—C13176.7 (4)
Mn1—O3—C8—C9142.0 (5)C10—C9—C14—C13−0.2 (6)
C20—O5—Mn1—O155.0 (3)C9—C10—C11—C121.1 (6)
C20—O5—Mn1—O2112.6 (3)Br2—C12—C11—C10−180.0 (3)
C20—O5—Mn1—O3−47.9 (3)C13—C12—C11—C10−0.9 (7)
C20—O5—Mn1—N1−150.8 (3)Br2—C12—C13—C14179.2 (3)
C20—O5—Mn1—C183.8 (3)C11—C12—C13—C140.2 (7)
Mn1—O5—C20—N2−15.3 (5)C9—C14—C13—C120.3 (6)
Mn1—O5—C20—C16i164.6 (2)N1—C15—C16—C17−2.1 (5)
C15—N1—Mn1—O192.4 (3)N1—C15—C16—C20i175.6 (3)
C15—N1—Mn1—O295.3 (3)C15—C16—C17—C180.2 (5)
C15—N1—Mn1—O3−80.9 (3)C20i—C16—C17—C18−177.4 (3)
C15—N1—Mn1—O57.7 (3)C19—C18—C17—C161.0 (6)
C15—N1—Mn1—O6−178.2 (3)N1—C19—C18—C17−0.3 (6)
C15—N1—Mn1—C195.2 (3)
Symmetry codes: (i) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2ii0.85 (3)2.02 (3)2.856 (4)168 (5)
O6—H6A···O1iii0.84 (5)1.96 (6)2.771 (4)162 (5)
O6—H6B···O4iii0.84 (4)1.83 (4)2.670 (4)175 (4)
C15—H15···O50.932.403.032 (4)125
C17—H17···O2iv0.932.273.125 (5)152
C19—H19···O60.932.533.129 (5)123
Symmetry codes: (ii) x−1, y, z; (iii) −x, −y, −z+1; (iv) −x+1, −y+1, −z+1.
Table 1
Selected geometric parameters (Å) top
Mn1—O12.316 (2)Mn1—O52.217 (2)
Mn1—O22.237 (2)Mn1—O62.170 (2)
Mn1—O32.025 (3)Mn1—N12.272 (3)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.85 (3)2.02 (3)2.856 (4)168 (5)
O6—H6A···O1ii0.84 (5)1.96 (6)2.771 (4)162 (5)
O6—H6B···O4ii0.84 (4)1.83 (4)2.670 (4)175 (4)
C17—H17···O2iii0.932.273.125 (5)152
Symmetry codes: (i) x−1, y, z; (ii) −x, −y, −z+1; (iii) −x+1, −y+1, −z+1.
Acknowledgements top

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the X-ray diffractometer. This work was supported financially by the Scientific and Technological Research Council of Turkey (grant No. 106 T472).

references
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