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Acta Cryst. (2007). E63, m2127    [ doi:10.1107/S1600536807033302 ]

Bis(benzoato-[kappa]2O,O')(2,9-dimethyl-1,10-phenanthroline-[kappa]2N,N')manganese(II)

P.-Z. Zhao, X.-P. Xuan and J.-G. Wang

Abstract top

In the title compound, [Mn(C7H5O2)2(C14H12N2)], the MnII ion is located on a twofold rotation axis and is coordinated by a bidentate 2,9-dimethyl-1,10-phenanthroline ligand and two bidentate benzoate anions in a distorted octahedral environment. The phenyl ring is disordered over two positions, with site occupancy factors of ca 0.57 and 0.43. The crystal packing is stabilized by [pi]-[pi] interactions between the 2,9-dimethyl-1,10-phenanthroline rings of neighboring molecules, with a distance between their ring planes of 3.443 Å.

Comment top

It is general believed that manganese plays an important role in biological systems (Ruttingter & Dismukes, 1997). In addition, metal-phenanthroline complexes and their derivatives have attracted much attention because of their peculiar features (Wang et al., 1996; Wall et al., 1999; Naing et al., 1995). The title complex, (I), was recently obtained from the reaction of 2,9-dimethyl-1,10-phenanthroline, sodium benzoate and Mn(NO3)2 in an ethanol/water mixture. Here we report its structure.

Each MnII ion is located on a twofold symmetry axis and is six-coordinated by two N atoms from a 2,9-dimethyl-1,10-phenanthroline ligand, and four O atoms from two benzoate anions. The MnO4N2 unit forms a distorted octahedron geometry, with two O atoms occupying the axial positions with the axial O—Mn—O angle 168.60 (7)° (Fig.1). The Mn—N bond length is 2.2360 (13)Å and the Mn—O bond lengths are 2.1611 (13) and 2.2971 (14)Å respectively

In the crystal structure, molecules are linked into a one dimensional network by π-π interactions between the 2,9-dimethyl-1,10-phenanthroline ring systems (Fig. 2). These intermolecular interactions occur between the parallel rings within offset face-to-face packing. The distance of neighboring molecules parallel ring planes is 3.4432 Å.

Related literature top

For related literature, see: Wang et al. (1996); Wall et al. (1999); Naing et al. (1995); Xuan et al. (2007).

For related literature, see: Ruttingter & Dismukes (1997).

Experimental top

To a solution of 2,9-dimethyl-1,10-phenanthroline hemihydrate (C14H12N20.5H2O, 0.109 g, 0.5 mmol) in ethanol(10 ml) and sodium benzoate (0.073 g, 0.5 mmol) in 1:1 (v/v) ethanol/water (20 ml) was added a 0.205 g 50% solution of Mn(NO3)2 (0.089 g, 0.5 mmol) in distilled water(5 ml). The mixture solution was stirred and refluxed for 4 h at 333 K. The hot solution was then filtered into a bottle. Yellow single crystals of (I) were appeared over a period of one week by slow evaporation at room temperature.

Refinement top

The H atoms were positioned geometrically and treated as riding, with C—H distances in the range 0.95–0.99Å and with Uiso(H) = 1.2Ueq(C). The disordered benzene ring has been put into two parts and site occupation refined. 93 least-squares restraints were used to the benzene ring to get reasonable shape and Ueq.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular stucture of the title complex(I),with atome labels and 30% probability displacement ellipsoids for non-H atoms. Symmetry code for the symbol 'A': -x + 2, y, -z + 1/2
[Figure 2] Fig. 2. The π-π interaction between 2,9-dimethyl-1,10-phenanthroline ligands in the crystal structure of (I). H atoms have been omitted for clarity.
Bis(benzoato-κ2O,O')(2,9-dimethyl-1,10-phenanthroline-\ κ2N,N')manganese(II) top
Crystal data top
[Mn(C7H5O2)2(C14H12N2)]F(000) = 1044
Mr = 505.42Dx = 1.378 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3415 reflections
a = 17.7020 (19) Åθ = 2.3–26.5°
b = 14.3903 (16) ŵ = 0.58 mm−1
c = 9.5678 (11) ÅT = 291 K
β = 91.431 (1)°Block, yellow
V = 2436.5 (5) Å30.43 × 0.24 × 0.21 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		2274 independent reflections
Radiation source: fine-focus sealed tube1940 reflections with I > 2σ(I)
graphiteRint = 0.020
φ and ω scansθmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		h = −20→21
Tmin = 0.789, Tmax = 0.886k = −17→17
9141 measured reflectionsl = −11→11
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0453P)2 + 1.3028P]
where P = (Fo2 + 2Fc2)/3
2274 reflections(Δ/σ)max = 0.002
179 parametersΔρmax = 0.25 e Å−3
93 restraintsΔρmin = −0.30 e Å−3
Crystal data top
[Mn(C7H5O2)2(C14H12N2)]V = 2436.5 (5) Å3
Mr = 505.42Z = 4
Monoclinic, C2/cMo Kα radiation
a = 17.7020 (19) ŵ = 0.58 mm−1
b = 14.3903 (16) ÅT = 291 K
c = 9.5678 (11) Å0.43 × 0.24 × 0.21 mm
β = 91.431 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2274 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		1940 reflections with I > 2σ(I)
Tmin = 0.789, Tmax = 0.886Rint = 0.020
9141 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.094Δρmax = 0.25 e Å−3
S = 1.06Δρmin = −0.30 e Å−3
2274 reflectionsAbsolute structure: ?
179 parametersFlack parameter: ?
93 restraintsRogers parameter: ?
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell e.s.d.'s are taken

into account individually in the estimation of e.s.d.'s in distances, angles

and torsion angles; correlations between e.s.d.'s in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F2, conventional R-factors R are based

on F, with F set to zero for negative F2. The threshold expression of

F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F2 are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C80.87920 (18)0.1290 (2)0.5538 (3)0.0514 (5)0.567 (2)
C90.8162 (2)0.1670 (3)0.6115 (3)0.0608 (6)0.567 (2)
H90.79960.22530.58200.073*0.567 (2)
C100.7767 (2)0.1203 (3)0.7128 (4)0.0759 (6)0.567 (2)
H100.73410.14690.75120.091*0.567 (2)
C110.8011 (2)0.0343 (3)0.7557 (4)0.0850 (11)0.567 (2)
H110.77480.00230.82350.102*0.567 (2)
C120.8638 (2)−0.0046 (3)0.7000 (4)0.0937 (11)0.567 (2)
H120.8802−0.06280.73020.112*0.567 (2)
C130.9028 (2)0.0422 (3)0.5988 (4)0.0749 (9)0.567 (2)
H130.94530.01520.56060.090*0.567 (2)
C8'0.8885 (3)0.1355 (2)0.5663 (4)0.0514 (5)0.433 (2)
C9'0.8128 (3)0.1519 (3)0.5892 (6)0.0608 (6)0.433 (2)
H9'0.78480.18940.52800.073*0.433 (2)
C10'0.7790 (3)0.1121 (4)0.7040 (6)0.0759 (6)0.433 (2)
H10'0.72810.12300.71960.091*0.433 (2)
C11'0.8198 (3)0.0572 (4)0.7940 (6)0.0850 (11)0.433 (2)
H11'0.79680.03090.87090.102*0.433 (2)
C12'0.8948 (3)0.0407 (4)0.7712 (5)0.0937 (11)0.433 (2)
H12'0.92240.00280.83250.112*0.433 (2)
C13'0.9296 (3)0.0801 (3)0.6571 (5)0.0749 (9)0.433 (2)
H13'0.98060.06900.64220.090*0.433 (2)
Mn11.00000.25641 (2)0.25000.05121 (11)
O10.99102 (8)0.15840 (10)0.41993 (15)0.0780 (4)
O20.89099 (8)0.24055 (9)0.37312 (15)0.0713 (4)
N10.94460 (7)0.37936 (9)0.14787 (12)0.0455 (3)
C10.88955 (9)0.37836 (13)0.04959 (17)0.0539 (4)
C20.86000 (10)0.46112 (15)−0.00559 (18)0.0633 (5)
H20.82200.4588−0.07440.076*
C30.88607 (11)0.54461 (14)0.04000 (18)0.0614 (5)
H30.86640.59920.00200.074*
C40.94303 (10)0.54831 (12)0.14496 (16)0.0518 (4)
C50.97064 (9)0.46279 (11)0.19584 (14)0.0434 (4)
C60.97268 (11)0.63307 (12)0.19948 (18)0.0636 (5)
H60.95420.68930.16510.076*
C70.86054 (12)0.28554 (16)0.0018 (2)0.0756 (6)
H7A0.90150.2496−0.03390.113*
H7B0.82260.2941−0.07050.113*
H7C0.83900.25350.07920.113*
C140.92396 (11)0.17951 (11)0.44429 (17)0.0541 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C80.0568 (11)0.0505 (10)0.0472 (9)0.0018 (8)0.0059 (8)0.0010 (8)
C90.0614 (11)0.0606 (14)0.0605 (14)0.0018 (10)0.0022 (10)−0.0056 (11)
C100.0597 (11)0.0969 (16)0.0718 (13)−0.0051 (11)0.0176 (10)−0.0054 (12)
C110.077 (2)0.111 (2)0.068 (2)−0.0111 (18)0.0173 (16)0.0230 (18)
C120.091 (2)0.102 (2)0.089 (2)0.0151 (19)0.0176 (18)0.0505 (18)
C130.0684 (18)0.079 (2)0.078 (2)0.0173 (15)0.0184 (15)0.0289 (16)
C8'0.0568 (11)0.0505 (10)0.0472 (9)0.0018 (8)0.0059 (8)0.0010 (8)
C9'0.0614 (11)0.0606 (14)0.0605 (14)0.0018 (10)0.0022 (10)−0.0056 (11)
C10'0.0597 (11)0.0969 (16)0.0718 (13)−0.0051 (11)0.0176 (10)−0.0054 (12)
C11'0.077 (2)0.111 (2)0.068 (2)−0.0111 (18)0.0173 (16)0.0230 (18)
C12'0.091 (2)0.102 (2)0.089 (2)0.0151 (19)0.0176 (18)0.0505 (18)
C13'0.0684 (18)0.079 (2)0.078 (2)0.0173 (15)0.0184 (15)0.0289 (16)
Mn10.0594 (2)0.0447 (2)0.0499 (2)0.0000.00940 (16)0.000
O10.0753 (8)0.0800 (9)0.0799 (9)0.0175 (7)0.0294 (7)0.0247 (7)
O20.0771 (9)0.0648 (8)0.0726 (8)0.0061 (6)0.0113 (7)0.0217 (6)
N10.0461 (7)0.0515 (7)0.0391 (6)−0.0034 (6)0.0057 (5)0.0023 (5)
C10.0464 (9)0.0705 (11)0.0450 (8)−0.0074 (8)0.0047 (7)0.0030 (8)
C20.0506 (9)0.0911 (14)0.0483 (9)0.0032 (9)0.0004 (8)0.0127 (9)
C30.0633 (11)0.0702 (11)0.0511 (9)0.0139 (9)0.0091 (8)0.0160 (8)
C40.0599 (10)0.0554 (9)0.0410 (8)0.0071 (8)0.0144 (7)0.0071 (7)
C50.0476 (8)0.0493 (8)0.0337 (7)0.0003 (7)0.0114 (6)0.0017 (6)
C60.0907 (14)0.0461 (9)0.0547 (10)0.0077 (9)0.0166 (9)0.0051 (7)
C70.0678 (12)0.0875 (14)0.0709 (12)−0.0233 (11)−0.0113 (10)−0.0018 (11)
C140.0697 (11)0.0424 (8)0.0506 (9)−0.0007 (8)0.0063 (8)−0.0035 (7)
Geometric parameters (Å, °) top
C8—C91.371 (5)Mn1—O12.1611 (13)
C8—C131.383 (5)Mn1—N12.2360 (13)
C8—C141.515 (4)Mn1—N1i2.2360 (13)
C9—C101.383 (5)Mn1—O2i2.2971 (14)
C9—H90.9300Mn1—O22.2972 (14)
C10—C111.370 (6)Mn1—C14i2.5723 (17)
C10—H100.9300Mn1—C142.5724 (17)
C11—C121.363 (6)O1—C141.253 (2)
C11—H110.9300O2—C141.247 (2)
C12—C131.379 (5)N1—C11.337 (2)
C12—H120.9300N1—C51.3616 (19)
C13—H130.9300C1—C21.399 (3)
C8'—C13'1.375 (6)C1—C71.498 (3)
C8'—C9'1.383 (7)C2—C31.355 (3)
C8'—C141.481 (5)C2—H20.9300
C9'—C10'1.388 (7)C3—C41.406 (2)
C9'—H9'0.9300C3—H30.9300
C10'—C11'1.363 (8)C4—C51.407 (2)
C10'—H10'0.9300C4—C61.422 (2)
C11'—C12'1.372 (7)C5—C5i1.449 (3)
C11'—H11'0.9300C6—C6i1.350 (4)
C12'—C13'1.388 (6)C6—H60.9300
C12'—H12'0.9300C7—H7A0.9600
C13'—H13'0.9300C7—H7B0.9600
Mn1—O1i2.1611 (13)C7—H7C0.9600
C9—C8—C13118.5 (3)O1—Mn1—C14i108.21 (5)
C9—C8—C14122.1 (3)N1—Mn1—C14i104.85 (5)
C13—C8—C14119.3 (3)N1i—Mn1—C14i115.12 (5)
C8—C9—C10121.2 (4)O2i—Mn1—C14i28.98 (5)
C8—C9—H9119.4O2—Mn1—C14i142.12 (6)
C10—C9—H9119.4O1i—Mn1—C14108.21 (5)
C11—C10—C9119.2 (4)O1—Mn1—C1429.07 (5)
C11—C10—H10120.4N1—Mn1—C14115.12 (5)
C9—C10—H10120.4N1i—Mn1—C14104.85 (5)
C12—C11—C10120.5 (4)O2i—Mn1—C14142.12 (6)
C12—C11—H11119.8O2—Mn1—C1428.98 (5)
C10—C11—H11119.8C14i—Mn1—C14129.04 (7)
C11—C12—C13120.1 (4)C14—O1—Mn193.99 (11)
C11—C12—H12120.0C14—O2—Mn187.84 (11)
C13—C12—H12120.0C1—N1—C5118.76 (14)
C12—C13—C8120.5 (3)C1—N1—Mn1127.07 (11)
C12—C13—H13119.8C5—N1—Mn1114.16 (10)
C8—C13—H13119.8N1—C1—C2121.02 (16)
C13'—C8'—C9'119.9 (4)N1—C1—C7117.53 (16)
C13'—C8'—C14121.2 (4)C2—C1—C7121.45 (16)
C9'—C8'—C14118.9 (4)C3—C2—C1120.80 (17)
C8'—C9'—C10'119.6 (5)C3—C2—H2119.6
C8'—C9'—H9'120.2C1—C2—H2119.6
C10'—C9'—H9'120.2C2—C3—C4119.73 (17)
C11'—C10'—C9'120.5 (5)C2—C3—H3120.1
C11'—C10'—H10'119.7C4—C3—H3120.1
C9'—C10'—H10'119.7C3—C4—C5116.79 (16)
C10'—C11'—C12'120.0 (5)C3—C4—C6123.10 (16)
C10'—C11'—H11'120.0C5—C4—C6120.11 (15)
C12'—C11'—H11'120.0N1—C5—C4122.88 (14)
C11'—C12'—C13'120.3 (5)N1—C5—C5i118.15 (8)
C11'—C12'—H12'119.8C4—C5—C5i118.96 (9)
C13'—C12'—H12'119.8C6i—C6—C4120.93 (10)
C8'—C13'—C12'119.7 (4)C6i—C6—H6119.5
C8'—C13'—H13'120.1C4—C6—H6119.5
C12'—C13'—H13'120.1C1—C7—H7A109.5
O1i—Mn1—O198.53 (8)C1—C7—H7B109.5
O1i—Mn1—N1103.14 (5)H7A—C7—H7B109.5
O1—Mn1—N1143.66 (5)C1—C7—H7C109.5
O1i—Mn1—N1i143.66 (5)H7A—C7—H7C109.5
O1—Mn1—N1i103.14 (5)H7B—C7—H7C109.5
N1—Mn1—N1i75.38 (7)O2—C14—O1120.11 (16)
O1i—Mn1—O2i58.05 (5)O2—C14—C8'122.0 (2)
O1—Mn1—O2i113.54 (5)O1—C14—C8'117.7 (2)
N1—Mn1—O2i102.68 (5)O2—C14—C8118.01 (19)
N1i—Mn1—O2i86.43 (4)O1—C14—C8121.78 (19)
O1i—Mn1—O2113.54 (5)C8'—C14—C88.4 (2)
O1—Mn1—O258.05 (5)O2—C14—Mn163.17 (10)
N1—Mn1—O286.43 (4)O1—C14—Mn156.94 (9)
N1i—Mn1—O2102.68 (5)C8'—C14—Mn1173.3 (2)
O2i—Mn1—O2168.59 (7)C8—C14—Mn1176.64 (15)
O1i—Mn1—C14i29.07 (5)
C13—C8—C9—C100.1 (2)N1—C1—C2—C3−0.5 (3)
C14—C8—C9—C10−179.1 (3)C7—C1—C2—C3179.08 (17)
C8—C9—C10—C11−0.1 (2)C1—C2—C3—C4−0.6 (3)
C9—C10—C11—C120.3 (4)C2—C3—C4—C50.8 (2)
C10—C11—C12—C13−0.4 (6)C2—C3—C4—C6−179.22 (17)
C11—C12—C13—C80.4 (5)C1—N1—C5—C4−1.0 (2)
C9—C8—C13—C12−0.3 (4)Mn1—N1—C5—C4−179.99 (11)
C14—C8—C13—C12179.0 (3)C1—N1—C5—C5i178.91 (16)
C13'—C8'—C9'—C10'0.0 (2)Mn1—N1—C5—C5i0.0 (2)
C14—C8'—C9'—C10'−179.2 (3)C3—C4—C5—N10.0 (2)
C8'—C9'—C10'—C11'0.0 (3)C6—C4—C5—N1−179.98 (14)
C9'—C10'—C11'—C12'−0.2 (5)C3—C4—C5—C5i−179.96 (16)
C10'—C11'—C12'—C13'0.4 (7)C6—C4—C5—C5i0.1 (3)
C9'—C8'—C13'—C12'0.2 (5)C3—C4—C6—C6i179.9 (2)
C14—C8'—C13'—C12'179.4 (4)C5—C4—C6—C6i−0.2 (3)
C11'—C12'—C13'—C8'−0.4 (6)Mn1—O2—C14—O10.18 (17)
O1i—Mn1—O1—C14−112.38 (12)Mn1—O2—C14—C8'175.0 (2)
N1—Mn1—O1—C1413.89 (16)Mn1—O2—C14—C8−176.45 (17)
N1i—Mn1—O1—C1497.00 (11)Mn1—O1—C14—O2−0.20 (18)
O2i—Mn1—O1—C14−171.16 (10)Mn1—O1—C14—C8'−175.22 (19)
O2—Mn1—O1—C140.11 (10)Mn1—O1—C14—C8176.31 (17)
C14i—Mn1—O1—C14−140.61 (10)C13'—C8'—C14—O2−169.1 (3)
O1i—Mn1—O2—C1485.24 (11)C9'—C8'—C14—O210.1 (4)
O1—Mn1—O2—C14−0.11 (10)C13'—C8'—C14—O15.8 (4)
N1—Mn1—O2—C14−171.97 (11)C9'—C8'—C14—O1−175.0 (2)
N1i—Mn1—O2—C14−97.83 (10)C13'—C8'—C14—C8126.9 (18)
O2i—Mn1—O2—C1444.60 (10)C9'—C8'—C14—C8−54.0 (17)
C14i—Mn1—O2—C1478.26 (16)C9—C8—C14—O2−23.5 (3)
O1i—Mn1—N1—C138.62 (13)C13—C8—C14—O2157.3 (2)
O1—Mn1—N1—C1−86.43 (15)C9—C8—C14—O1159.9 (2)
N1i—Mn1—N1—C1−178.83 (15)C13—C8—C14—O1−19.3 (3)
O2i—Mn1—N1—C198.32 (13)C9—C8—C14—C8'96.7 (17)
O2—Mn1—N1—C1−74.74 (13)C13—C8—C14—C8'−82.5 (17)
C14i—Mn1—N1—C168.55 (13)O1i—Mn1—C14—O2−105.89 (11)
C14—Mn1—N1—C1−79.02 (13)O1—Mn1—C14—O2179.81 (17)
O1i—Mn1—N1—C5−142.54 (10)N1—Mn1—C14—O28.85 (12)
O1—Mn1—N1—C592.42 (13)N1i—Mn1—C14—O289.41 (11)
N1i—Mn1—N1—C50.01 (7)O2i—Mn1—C14—O2−166.93 (8)
O2i—Mn1—N1—C5−82.83 (10)C14i—Mn1—C14—O2−129.28 (11)
O2—Mn1—N1—C5104.11 (10)O1i—Mn1—C14—O174.30 (14)
C14i—Mn1—N1—C5−112.61 (10)N1—Mn1—C14—O1−170.96 (11)
C14—Mn1—N1—C599.82 (10)N1i—Mn1—C14—O1−90.40 (11)
C5—N1—C1—C21.3 (2)O2i—Mn1—C14—O113.26 (15)
Mn1—N1—C1—C2−179.91 (11)O2—Mn1—C14—O1−179.81 (17)
C5—N1—C1—C7−178.30 (14)C14i—Mn1—C14—O150.91 (10)
Mn1—N1—C1—C70.5 (2)
Symmetry codes: (i) −x+2, y, −z+1/2.
references
References top

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