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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page m1026
https://doi.org/10.1107/S1600536812029364

trans-Bis(nitrato-κO)bis­­(1,10-phenanthroline-κ2N,N′)manganese(II)

Watcharin Saphu,a Songwuit Chanthee,a Kittipong Chainok,a* David J. Hardingb and Chaveng Pakawatchaic

aDepartment of Chemistry, Faculty of Science, Naresuan University, Muang, Phitsanulok 65000, Thailand, bMolecular Technology Research Unit, Department of Chemistry, Walailak University, Nakhon Si Thammarat 80161, Thailand, and cDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
*Correspondence e-mail: kittipongc@nu.ac.th

(Received 10 June 2012; accepted 27 June 2012; online 4 July 2012)

In the title compound, [Mn(NO3)2(C12H8N2)2], the MnII atom lies on a twofold rotation axis, and is six-coordinated in a distorted trans-N4O2 octa­hedral environment by four N atoms from two 1,10-phenanthroline ligands and two O atoms from two nitrate anions. The nitrate anion is disordered about a twofold rotation axis with fixed occupancy factors of 0.5. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds and π–π stacking inter­actions [centroid–centroid distance = 4.088 (5) Å] into a three-dimensional supra­molecular network.

Related literature

For the isotypic Cd compound, see: Shi et al. (2004[Shi, X., Zhu, G., Fang, Q., Wu, G., Tian, G., Wang, R., Zhang, D., Xue, M. & Qiu, S. (2004). Eur. J. Inorg. Chem. pp. 185-191.]).

[Scheme 1]

Experimental

Crystal data

  • [Mn(NO3)2(C12H8N2)2]

  • Mr = 539.37

  • Monoclinic, C 2/c

  • a = 11.6191 (6) Å

  • b = 15.1164 (8) Å

  • c = 13.4526 (7) Å

  • β = 105.387 (1)°

  • V = 2278.1 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.64 mm−1

  • T = 298 K

  • 0.33 × 0.15 × 0.07 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.819, Tmax = 1.000

  • 13250 measured reflections

  • 2748 independent reflections

  • 2367 reflections with I > 2σ(I)

  • Rint = 0.028
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.101

  • S = 1.15

  • 2748 reflections

  • 204 parameters

  • 60 restraints

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C3—H3⋯O1Ai 0.93 2.40 3.232 (9) 148
C3—H3⋯O1Bi 0.93 2.40 3.214 (10) 146
C7—H7⋯O2Aii 0.93 2.29 3.101 (8) 146
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). 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: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812029364/ng5277sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029364/ng5277Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029364/ng5277Isup3.cdx

checkCIF report


Comment top

The mononuclear metal complexes of the chelating bidentate 1,10-phenanthroline (phen) and 2,2'-bipyridine (bipy) ligands are well known in the literature, and have been used in many fields. In the realm of coordination polymers, these complexes have been employed as coordination acceptor nodes for the construction of low dimensional polymer-based magnets exhibiting long-range magnetic ordering and spin crossover transitions. This communication forms part of our study of the synthesis and magnetic properties of one dimensional tube-like cyanide-bridged bimetallic coordination polymers. The main strategy of the proposed tube motif is to combine two building blocks involving one coordination donor, the chelated tetracyanoferrate, [Fe(L)(CN)4]x- (x = 1 or 2), and a coordination acceptor, [M(L)S] (where M = an octahedral metal; L = bipy or phen, S = solvents or counter ions). Here, we describe the crystal structure of a building block trans-[Mn(phen)2(NO3)2] (I), which is a new member of the mononuclear metal complexes with chelating bidentate ligands.

Compound I is isostructural with the Cd analog (Shi et al., 2004). It crystallizes in a monoclinic system in the space group C2/c, and contains half of the complex molecule per asymmetric unit, Fig. 1. The MnII atom lies on a twofold rotation axis, and is six-coordinate in a distorted trans-MnN4O2 octahedral environment by two O atoms from two disordered [NO3]– anions and four N atoms from two phen ligands. The dihedral angle between the least-squares planes of the two phen ligands [maximum deviation = 0.036 (1) Å] is 25.01 (5)°.

In the crystal, molecules are assembled into one dimensional supramolecular chains parallel to the c axis through weak π–π stacking between adjacent aromatic rings of the phen ligands with a centroid-centroid distance of 4.088 (5) Å, Fig. 2. Weak C—H···O hydrogen bonds involving the phen ligands and the [NO3]– anions, Table 1, are further linked to neighboring chains into a three dimensional supramolecular network along the a axis, Fig. 3.

Related literature top

For the isotypic Cd compound, see: Shi et al. (2004).

Experimental top

A methanol solution (5 ml) of phen (20.0 mg, 0.1 mmol) was added dropwise to a methanol solution (5 ml) of Mn(NO3)2.4H2O (30.0 mg, 0.1 mmol) with constant stirring 1 h and filtered to remove any undissolved solid. The filtrate was allowed to stand to slowly evaporate, at room temperature. After one week, yellow blocks of I were obtained (Yield 23 mg, 88% based on Mn source). IR υmax(cm-1): 722 s, 768w, 780w, 821w, 842m, 853w, 863w, 1017m, 1048w, 1101w, 1141br, 1223w, 1290m, 1325m, 1408w, 1427w, 1459w, 1518m, 1578w, 1624w, 3059br. UV-Vis (CH3OH/H2O), λmax = 265 nm.

Refinement top

The C-bound hydrogen atoms were placed in geometrically idealized positions based on chemical coordinations and constrained to ride on their parent atom positions with a C–H distances of 0.93 Å and with Uiso(H) = 1.2Ueq(C) for the aromatic H atoms. The nitrate anions are disordered about a twofold rotation axis and were refined using a two site model. The site occupancy factors for the two orientations were then fixed to 0.5. The nitrogen-oxygen distances were restrained to 1.24 ± 0.01 Å and O···O of 2.15 Å, however, the anisotropic temperature factors were restrained to be nearly isotropic.

Structure description top

The mononuclear metal complexes of the chelating bidentate 1,10-phenanthroline (phen) and 2,2'-bipyridine (bipy) ligands are well known in the literature, and have been used in many fields. In the realm of coordination polymers, these complexes have been employed as coordination acceptor nodes for the construction of low dimensional polymer-based magnets exhibiting long-range magnetic ordering and spin crossover transitions. This communication forms part of our study of the synthesis and magnetic properties of one dimensional tube-like cyanide-bridged bimetallic coordination polymers. The main strategy of the proposed tube motif is to combine two building blocks involving one coordination donor, the chelated tetracyanoferrate, [Fe(L)(CN)4]x- (x = 1 or 2), and a coordination acceptor, [M(L)S] (where M = an octahedral metal; L = bipy or phen, S = solvents or counter ions). Here, we describe the crystal structure of a building block trans-[Mn(phen)2(NO3)2] (I), which is a new member of the mononuclear metal complexes with chelating bidentate ligands.

Compound I is isostructural with the Cd analog (Shi et al., 2004). It crystallizes in a monoclinic system in the space group C2/c, and contains half of the complex molecule per asymmetric unit, Fig. 1. The MnII atom lies on a twofold rotation axis, and is six-coordinate in a distorted trans-MnN4O2 octahedral environment by two O atoms from two disordered [NO3]– anions and four N atoms from two phen ligands. The dihedral angle between the least-squares planes of the two phen ligands [maximum deviation = 0.036 (1) Å] is 25.01 (5)°.

In the crystal, molecules are assembled into one dimensional supramolecular chains parallel to the c axis through weak π–π stacking between adjacent aromatic rings of the phen ligands with a centroid-centroid distance of 4.088 (5) Å, Fig. 2. Weak C—H···O hydrogen bonds involving the phen ligands and the [NO3]– anions, Table 1, are further linked to neighboring chains into a three dimensional supramolecular network along the a axis, Fig. 3.

For the isotypic Cd compound, see: Shi et al. (2004).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot of a fragment at the 30% probability level containing the asymmetric unit with atom numbering and coordination environment of the metal centers of I.
[Figure 2] Fig. 2. The one dimensional supramolecular chain linked by intermolecular π–π stacking interactions in I.
[Figure 3] Fig. 3. The stacking plot of I, showing H-bond interactions (dashed lines) and π–π stacking interactions along the a axis.
trans-Bis(nitrato-κO)bis(1,10-phenanthroline- κ2N,N')manganese(II) top
Crystal data top
[Mn(NO3)2(C12H8N2)2]F(000) = 1100
Mr = 539.37Dx = 1.573 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 11.6191 (6) ÅCell parameters from 3448 reflections
b = 15.1164 (8) Åθ = 2.5–23.1°
c = 13.4526 (7) ŵ = 0.64 mm−1
β = 105.387 (1)°T = 298 K
V = 2278.1 (2) Å3Block, yellow
Z = 40.33 × 0.15 × 0.07 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		2748 independent reflections
Radiation source: fine-focus sealed tube2367 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 8 pixels mm-1θmax = 28.1°, θmin = 2.3°
ω and φ scansh = −15→15
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −20→20
Tmin = 1.000, Tmax = 0.819l = −17→17
13250 measured reflections
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.0483P)2 + 0.5759P]
where P = (Fo2 + 2Fc2)/3
2748 reflections(Δ/σ)max < 0.001
204 parametersΔρmax = 0.32 e Å−3
60 restraintsΔρmin = −0.19 e Å−3
Crystal data top
[Mn(NO3)2(C12H8N2)2]V = 2278.1 (2) Å3
Mr = 539.37Z = 4
Monoclinic, C2/cMo Kα radiation
a = 11.6191 (6) ŵ = 0.64 mm−1
b = 15.1164 (8) ÅT = 298 K
c = 13.4526 (7) Å0.33 × 0.15 × 0.07 mm
β = 105.387 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2748 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2367 reflections with I > 2σ(I)
Tmin = 1.000, Tmax = 0.819Rint = 0.028
13250 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04560 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.15Δρmax = 0.32 e Å−3
2748 reflectionsΔρmin = −0.19 e Å−3
204 parameters
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)
Mn10.50000.53331 (2)0.25000.04311 (14)
O2B0.6274 (5)0.4964 (4)0.4166 (6)0.0606 (12)0.50
N3B0.7282 (5)0.5186 (4)0.4076 (6)0.039 (2)0.50
N10.58698 (13)0.41378 (9)0.19902 (11)0.0433 (3)
C10.67011 (17)0.41303 (13)0.14807 (15)0.0509 (4)
H10.69930.46700.13220.061*
N20.46192 (14)0.65384 (10)0.33693 (12)0.0470 (4)
C20.71604 (18)0.33619 (14)0.11701 (17)0.0575 (5)
H20.77260.33900.07950.069*
C30.67701 (19)0.25688 (14)0.14224 (18)0.0608 (5)
H30.70770.20470.12310.073*
C40.59018 (18)0.25400 (12)0.19736 (16)0.0533 (5)
C50.54589 (15)0.33464 (11)0.22300 (14)0.0423 (4)
C60.5430 (2)0.17310 (14)0.2252 (2)0.0742 (7)
H60.57240.11950.20850.089*
C70.42093 (19)0.65392 (15)0.41958 (16)0.0584 (5)
H70.40960.59980.44850.070*
C80.3938 (2)0.73067 (18)0.46553 (18)0.0684 (6)
H80.36320.72750.52270.082*
C90.4125 (2)0.81020 (16)0.42592 (17)0.0702 (7)
H90.39570.86220.45640.084*
C100.45699 (18)0.81377 (13)0.33906 (16)0.0571 (5)
C110.47871 (16)0.73301 (11)0.29567 (14)0.0438 (4)
C120.4796 (2)0.89451 (13)0.29208 (19)0.0760 (7)
H120.46580.94820.32070.091*
O1A0.6994 (7)0.5637 (6)0.3267 (6)0.087 (3)0.50
N3A0.7310 (8)0.5230 (6)0.4089 (7)0.077 (4)0.50
O2A0.6590 (8)0.4707 (6)0.4282 (7)0.136 (4)0.50
O3A0.8353 (6)0.5253 (5)0.4576 (7)0.0747 (19)0.50
O1B0.7286 (8)0.5562 (6)0.3270 (6)0.096 (3)0.50
O3B0.8112 (7)0.5128 (8)0.4831 (6)0.105 (4)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0543 (2)0.02415 (19)0.0546 (3)0.0000.02096 (18)0.000
O2B0.0571 (19)0.063 (2)0.065 (3)0.0025 (19)0.0224 (17)0.0032 (19)
N3B0.038 (4)0.020 (3)0.060 (6)0.008 (2)0.017 (3)−0.003 (3)
N10.0468 (8)0.0325 (7)0.0534 (8)0.0005 (6)0.0183 (6)0.0011 (6)
C10.0518 (10)0.0441 (10)0.0614 (11)0.0033 (8)0.0229 (9)0.0061 (8)
N20.0570 (9)0.0363 (8)0.0506 (9)0.0010 (6)0.0194 (7)−0.0003 (6)
C20.0534 (11)0.0563 (12)0.0691 (13)0.0114 (9)0.0276 (10)0.0016 (10)
C30.0657 (12)0.0451 (11)0.0764 (14)0.0169 (9)0.0273 (11)−0.0039 (10)
C40.0608 (11)0.0340 (9)0.0666 (12)0.0068 (8)0.0193 (10)0.0004 (8)
C50.0471 (9)0.0308 (8)0.0489 (10)0.0011 (7)0.0128 (8)0.0004 (7)
C60.0909 (18)0.0293 (10)0.112 (2)0.0061 (10)0.0432 (15)−0.0026 (11)
C70.0636 (12)0.0593 (13)0.0563 (12)−0.0013 (9)0.0229 (10)0.0002 (9)
C80.0662 (13)0.0844 (18)0.0570 (12)0.0140 (12)0.0206 (10)−0.0108 (12)
C90.0742 (14)0.0644 (15)0.0671 (14)0.0244 (11)0.0100 (11)−0.0214 (11)
C100.0616 (12)0.0383 (10)0.0639 (12)0.0112 (8)0.0032 (10)−0.0098 (9)
C110.0459 (9)0.0308 (8)0.0515 (10)0.0020 (7)0.0075 (7)−0.0021 (7)
C120.0973 (18)0.0293 (10)0.0893 (17)0.0069 (10)0.0033 (14)−0.0102 (9)
O1A0.091 (4)0.043 (3)0.097 (6)−0.012 (2)−0.027 (3)0.015 (3)
N3A0.099 (9)0.068 (6)0.069 (8)−0.030 (5)0.031 (7)−0.036 (5)
O2A0.191 (8)0.154 (8)0.083 (5)−0.117 (6)0.070 (6)−0.023 (5)
O3A0.062 (3)0.065 (3)0.088 (4)0.013 (2)0.003 (3)−0.016 (3)
O1B0.154 (7)0.075 (5)0.085 (5)−0.060 (4)0.076 (5)−0.021 (3)
O3B0.062 (3)0.162 (8)0.085 (5)0.027 (4)0.004 (3)−0.050 (5)
Geometric parameters (Å, º) top
Mn1—N12.2636 (14)C3—H30.9300
Mn1—N1i2.2636 (14)C4—C51.401 (2)
Mn1—N22.2711 (15)C4—C61.430 (3)
Mn1—N2i2.2712 (15)C5—C5i1.441 (3)
Mn1—O1A2.318 (8)C6—C6i1.340 (5)
Mn1—O1Ai2.318 (8)C6—H60.9300
Mn1—O2Bi2.401 (7)C7—C81.389 (3)
Mn1—O2B2.401 (7)C7—H70.9300
O2B—N3B1.255 (6)C8—C91.356 (4)
N3B—O3B1.204 (7)C8—H80.9300
N3B—O1B1.225 (6)C9—C101.399 (3)
N1—C11.324 (2)C9—H90.9300
N1—C51.358 (2)C10—C111.405 (2)
C1—C21.388 (3)C10—C121.431 (3)
C1—H10.9300C11—C11i1.441 (4)
N2—C71.321 (2)C12—C12i1.338 (5)
N2—C111.355 (2)C12—H120.9300
C2—C31.357 (3)O1A—N3A1.233 (7)
C2—H20.9300N3A—O3A1.216 (7)
C3—C41.402 (3)N3A—O2A1.227 (7)
N1—Mn1—N1i74.08 (7)C7—N2—Mn1126.68 (14)
N1—Mn1—N2163.74 (5)C11—N2—Mn1115.38 (12)
N1i—Mn1—N2108.71 (5)C3—C2—C1118.91 (19)
N1—Mn1—N2i108.71 (5)C3—C2—H2120.5
N1i—Mn1—N2i163.74 (5)C1—C2—H2120.5
N2—Mn1—N2i73.31 (8)C2—C3—C4119.66 (18)
N1—Mn1—O1A79.6 (3)C2—C3—H3120.2
N1i—Mn1—O1A119.80 (18)C4—C3—H3120.2
N2—Mn1—O1A85.4 (3)C5—C4—C3117.76 (17)
N2i—Mn1—O1A76.24 (18)C5—C4—C6119.20 (19)
N1—Mn1—O1Ai119.80 (18)C3—C4—C6123.00 (18)
N1i—Mn1—O1Ai79.6 (3)N1—C5—C4122.18 (16)
N2—Mn1—O1Ai76.24 (18)N1—C5—C5i118.26 (9)
N2i—Mn1—O1Ai85.4 (3)C4—C5—C5i119.56 (11)
O1A—Mn1—O1Ai157.2 (4)C6i—C6—C4121.23 (12)
N1—Mn1—O2Bi75.28 (17)C6i—C6—H6119.4
N1i—Mn1—O2Bi83.30 (16)C4—C6—H6119.4
N2—Mn1—O2Bi120.73 (17)N2—C7—C8123.4 (2)
N2i—Mn1—O2Bi82.05 (17)N2—C7—H7118.3
O1A—Mn1—O2Bi139.2 (3)C8—C7—H7118.3
O1Ai—Mn1—O2Bi48.3 (3)C9—C8—C7119.1 (2)
N1—Mn1—O2B83.30 (16)C9—C8—H8120.4
N1i—Mn1—O2B75.28 (17)C7—C8—H8120.4
N2—Mn1—O2B82.04 (17)C8—C9—C10119.7 (2)
N2i—Mn1—O2B120.73 (17)C8—C9—H9120.1
O1A—Mn1—O2B48.3 (3)C10—C9—H9120.1
O1Ai—Mn1—O2B139.2 (3)C9—C10—C11117.4 (2)
O2Bi—Mn1—O2B153.1 (3)C9—C10—C12123.7 (2)
N3B—O2B—Mn1102.0 (5)C11—C10—C12118.9 (2)
O3B—N3B—O1B126.1 (7)N2—C11—C10122.41 (18)
O3B—N3B—O2B117.3 (7)N2—C11—C11i117.94 (10)
O1B—N3B—O2B115.6 (6)C10—C11—C11i119.64 (12)
C1—N1—C5117.77 (15)C12i—C12—C10121.45 (13)
C1—N1—Mn1127.53 (12)C12i—C12—H12119.3
C5—N1—Mn1114.70 (11)C10—C12—H12119.3
N1—C1—C2123.67 (18)N3A—O1A—Mn1108.9 (7)
N1—C1—H1118.2O3A—N3A—O2A122.9 (9)
C2—C1—H1118.2O3A—N3A—O1A119.0 (9)
C7—N2—C11117.87 (17)O2A—N3A—O1A117.0 (9)
N1—Mn1—O2B—N3B72.3 (5)N1—C1—C2—C3−2.0 (3)
N1i—Mn1—O2B—N3B147.6 (5)C1—C2—C3—C41.0 (3)
N2—Mn1—O2B—N3B−100.6 (5)C2—C3—C4—C50.9 (3)
N2i—Mn1—O2B—N3B−35.5 (5)C2—C3—C4—C6178.8 (2)
O1A—Mn1—O2B—N3B−9.7 (5)C1—N1—C5—C41.2 (3)
O1Ai—Mn1—O2B—N3B−158.6 (5)Mn1—N1—C5—C4−179.84 (14)
O2Bi—Mn1—O2B—N3B109.4 (5)C1—N1—C5—C5i−179.05 (19)
Mn1—O2B—N3B—O3B175.4 (8)Mn1—N1—C5—C5i−0.1 (3)
Mn1—O2B—N3B—O1B5.9 (9)C3—C4—C5—N1−2.1 (3)
N1i—Mn1—N1—C1178.83 (19)C6—C4—C5—N1179.9 (2)
N2—Mn1—N1—C1−78.8 (3)C3—C4—C5—C5i178.2 (2)
N2i—Mn1—N1—C115.61 (17)C6—C4—C5—C5i0.2 (3)
O1A—Mn1—N1—C1−55.9 (2)C5—C4—C6—C6i0.3 (5)
O1Ai—Mn1—N1—C1111.2 (3)C3—C4—C6—C6i−177.7 (3)
O2Bi—Mn1—N1—C191.7 (2)C11—N2—C7—C80.4 (3)
O2B—Mn1—N1—C1−104.6 (2)Mn1—N2—C7—C8−176.49 (16)
N1i—Mn1—N1—C50.05 (9)N2—C7—C8—C9−1.6 (4)
N2—Mn1—N1—C5102.4 (2)C7—C8—C9—C100.8 (3)
N2i—Mn1—N1—C5−163.17 (12)C8—C9—C10—C111.0 (3)
O1A—Mn1—N1—C5125.4 (2)C8—C9—C10—C12−179.9 (2)
O1Ai—Mn1—N1—C5−67.6 (3)C7—N2—C11—C101.6 (3)
O2Bi—Mn1—N1—C5−87.1 (2)Mn1—N2—C11—C10178.82 (14)
O2B—Mn1—N1—C576.6 (2)C7—N2—C11—C11i−178.8 (2)
C5—N1—C1—C20.8 (3)Mn1—N2—C11—C11i−1.6 (3)
Mn1—N1—C1—C2−177.93 (15)C9—C10—C11—N2−2.3 (3)
N1—Mn1—N2—C7−82.9 (3)C12—C10—C11—N2178.55 (19)
N1i—Mn1—N2—C714.44 (18)C9—C10—C11—C11i178.2 (2)
N2i—Mn1—N2—C7177.5 (2)C12—C10—C11—C11i−1.0 (3)
O1A—Mn1—N2—C7−105.5 (2)C9—C10—C12—C12i−178.8 (3)
O1Ai—Mn1—N2—C788.2 (3)C11—C10—C12—C12i0.3 (4)
O2Bi—Mn1—N2—C7107.8 (2)N1—Mn1—O1A—N3A−82.7 (8)
O2B—Mn1—N2—C7−57.0 (2)N1i—Mn1—O1A—N3A−17.9 (9)
N1—Mn1—N2—C11100.2 (2)N2—Mn1—O1A—N3A91.0 (8)
N1i—Mn1—N2—C11−162.48 (12)N2i—Mn1—O1A—N3A164.9 (8)
N2i—Mn1—N2—C110.58 (9)O1Ai—Mn1—O1A—N3A127.4 (8)
O1A—Mn1—N2—C1177.6 (2)O2Bi—Mn1—O1A—N3A−135.2 (7)
O1Ai—Mn1—N2—C11−88.7 (3)O2B—Mn1—O1A—N3A7.6 (7)
O2Bi—Mn1—N2—C11−69.2 (2)Mn1—O1A—N3A—O3A175.0 (8)
O2B—Mn1—N2—C11126.1 (2)Mn1—O1A—N3A—O2A6.7 (13)
Symmetry code: (i) −x+1, y, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1Aii0.932.403.232 (9)148
C3—H3···O1Bii0.932.403.214 (10)146
C7—H7···O2Aiii0.932.293.101 (8)146
Symmetry codes: (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula[Mn(NO3)2(C12H8N2)2]
Mr539.37
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)11.6191 (6), 15.1164 (8), 13.4526 (7)
β (°) 105.387 (1)
V (Å3)2278.1 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.64
Crystal size (mm)0.33 × 0.15 × 0.07
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax1.000, 0.819
No. of measured, independent and
observed [I > 2σ(I)] reflections		13250, 2748, 2367
Rint0.028
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.101, 1.15
No. of reflections2748
No. of parameters204
No. of restraints60
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.32, −0.19

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1Ai0.932.403.232 (9)148.3
C3—H3···O1Bi0.932.403.214 (10)145.8
C7—H7···O2Aii0.932.293.101 (8)146.0
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1.
 

Acknowledgements

We thank the Thailand Research Fund for funding this work (project No. MRG5480189).

References

First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationShi, X., Zhu, G., Fang, Q., Wu, G., Tian, G., Wang, R., Zhang, D., Xue, M. & Qiu, S. (2004). Eur. J. Inorg. Chem. pp. 185–191.  Web of Science CSD CrossRef CAS Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page m1026
https://doi.org/10.1107/S1600536812029364
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