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

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ISSN: 2056-9890

Bis(3-carb­­oxy-5-nitro­benzoato)bis­­[2-(pyridin-4-yl)-1H-imidazo[4,5-f][1,10]phenanthroline]manganese(II)

aChina Science and Technology Exchange Center, Ministry of Science and Technology, Beijing 100045, People's Republic of China, and bCollege of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China
*Correspondence e-mail: xuhongbin2001@yahoo.com.cn

(Received 6 February 2011; accepted 7 February 2011; online 12 February 2011)

In the title compound, [Mn(C8H4NO6)2(C18H11N5)2], the MnII atom is six-coordinated by two N,N′-bidentate 6-(pyridin-4-yl)-5H-cyclo­penta­[f][1,10]phenanthroline (pcp) ligands and two carboxyl­ate O atoms from two monodentate 3-carb­oxy-5-nitro­benzoate anions in a distorted cis-MnO2N4 octa­hedral arrangement. Within the pcp ligands, the dihedral angles between the polycyclic skeletons and pendant pyridine rings are 6.2 (2) and 8.3 (2)°. In the crystal, mol­ecules are linked by O—H⋯N and N—H⋯O hydrogen bonds. Several aromatic ππ stacking inter­actions [shortest centroid–centroid separation = 3.516 (3) Å] are also observed.

Related literature

For background to ligands based on 1,10-phenanthroline, see: Wang et al. (2010[Wang, X. Y., Ma, X. Y., Liu, Y., Xu, Z. L. & Kong, Z. G. (2010). Chin. J. Inorg. Chem. 26, 1482-1484.]).

[Scheme 1]

Experimental

Crystal data
  • [Mn(C8H4NO6)2(C18H11N5)2]

  • Mr = 1069.82

  • Monoclinic, P 2/n

  • a = 21.791 (3) Å

  • b = 8.2215 (12) Å

  • c = 27.270 (4) Å

  • β = 111.767 (3)°

  • V = 4537.2 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.38 mm−1

  • T = 293 K

  • 0.22 × 0.18 × 0.16 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.45, Tmax = 0.69

  • 22806 measured reflections

  • 8037 independent reflections

  • 3602 reflections with I > 2σ(I)

  • Rint = 0.105

Refinement
  • R[F2 > 2σ(F2)] = 0.065

  • wR(F2) = 0.126

  • S = 0.95

  • 8037 reflections

  • 694 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Selected geometric parameters (Å, °)

Mn1—O1 2.142 (3)
Mn1—O6 2.142 (3)
Mn1—N1 2.339 (4)
Mn1—N2 2.220 (3)
Mn1—N6 2.221 (4)
Mn1—N7 2.309 (4)
N6—Mn1—N7 72.19 (14)
N2—Mn1—N1 72.42 (13)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O7—H9A⋯N10i 0.82 1.81 2.629 (5) 176
O4—H4⋯N5ii 0.82 1.82 2.636 (5) 173
N9—H7A⋯O2iii 0.86 1.94 2.789 (5) 171
N4—H4A⋯O5iv 0.86 1.89 2.745 (5) 171
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]; (iii) -x+2, -y+1, -z+1; (iv) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). 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: SHELXL97.

Supporting information


Comment top

The coordination complexes based on 1,10-phenanthroline-like ligands have received intense interests of chemists (Wang et al., 2010). The (6-(pyridin-4-yl)-5H-cyclopenta[f][1,10]phenanthroline ligand (L), as a good candidate for N-donor ligand, has excellent coordinating ability. In this work, we selected 1,3-Hbdc ligand (1,3-Hbdc = 5-nitro-benzene-1-carboxylate-3-carboxylic acid) as a secondary ligand and L as a N-donor chelating ligand, generating a new molecular MnII complex, [Mn(L)2(1,3-Hbdc)2].

The central MnII atom is six-coordinated by four N atoms from two different L ligands, and two carboxylate O atoms from two different 1,3-Hbdc ligands in a distorted octahedral sphere. The O—H···N and N—H···O H-bonding interactions further stabilize the structure of (I).

Related literature top

For background to ligands based on 1,10-phenanthroline, see: Wang et al. (2010).

Experimental top

A mixture of MnCl2.4H2O (0.5 mmol), 1,3-H2bdc (0.5 mmol) and L (0.5 mmol) in 1 ml distilled water was heated at 460 K in a Teflon-lined stainless steel autoclave for seven days. The reaction system was then slowly cooled to room temperature. Pale yellow blocks of (I) were collected from the final reaction system by filtration, washed several times with distilled water and dried in air at ambient temperature. Yield: 31% based on Mn(II).

Refinement top

All H atoms were positioned geometrically (C–H = 0.93 Å) and refined as riding, with Uiso(H) = 1.2Ueq(carrier).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit in (I) with isplacement ellipsoids drawn at the 30% probability level.
Bis(3-carboxy-5-nitrobenzoato)bis[2-(pyridin-4-yl)-1H-imidazo[4,5-f][1,10]phenanthroline]manganese(II) top
Crystal data top
[Mn(C8H4NO6)2(C18H11N5)2]F(000) = 2188
Mr = 1069.82Dx = 1.566 Mg m3
Monoclinic, P2/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yacCell parameters from 8037 reflections
a = 21.791 (3) Åθ = 1.5–25.1°
b = 8.2215 (12) ŵ = 0.38 mm1
c = 27.270 (4) ÅT = 293 K
β = 111.767 (3)°Block, pale yellow
V = 4537.2 (12) Å30.22 × 0.18 × 0.16 mm
Z = 4
Data collection top
Bruker APEX CCD
diffractometer
8037 independent reflections
Radiation source: fine-focus sealed tube3602 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.105
ϕ and ω scansθmax = 25.1°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2525
Tmin = 0.45, Tmax = 0.69k = 99
22806 measured reflectionsl = 3231
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0333P)2]
where P = (Fo2 + 2Fc2)/3
8037 reflections(Δ/σ)max = 0.001
694 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
[Mn(C8H4NO6)2(C18H11N5)2]V = 4537.2 (12) Å3
Mr = 1069.82Z = 4
Monoclinic, P2/nMo Kα radiation
a = 21.791 (3) ŵ = 0.38 mm1
b = 8.2215 (12) ÅT = 293 K
c = 27.270 (4) Å0.22 × 0.18 × 0.16 mm
β = 111.767 (3)°
Data collection top
Bruker APEX CCD
diffractometer
8037 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3602 reflections with I > 2σ(I)
Tmin = 0.45, Tmax = 0.69Rint = 0.105
22806 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 0.95Δρmax = 0.29 e Å3
8037 reflectionsΔρmin = 0.24 e Å3
694 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 > 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
C10.7839 (2)0.3222 (6)0.62459 (18)0.0436 (13)
H10.82080.26730.62370.052*
C20.7751 (2)0.3328 (6)0.67284 (18)0.0517 (14)
H20.80490.28400.70310.062*
C30.7218 (3)0.4161 (6)0.67451 (18)0.0493 (14)
H30.71510.42500.70620.059*
C40.6774 (2)0.4880 (5)0.62896 (18)0.0370 (12)
C50.6891 (2)0.4700 (5)0.58208 (17)0.0341 (12)
C60.6429 (2)0.5362 (5)0.53295 (18)0.0340 (12)
C70.5577 (3)0.6533 (6)0.43876 (19)0.0543 (15)
H70.52970.69110.40590.065*
C80.5446 (2)0.6859 (6)0.48274 (19)0.0478 (14)
H80.50780.74730.48050.057*
C90.6132 (3)0.5630 (6)0.44341 (19)0.0479 (14)
H90.62100.54010.41280.058*
C100.5871 (2)0.6262 (5)0.53116 (18)0.0350 (12)
C110.5787 (2)0.6459 (5)0.58042 (17)0.0348 (12)
C120.6213 (2)0.5789 (5)0.62744 (18)0.0386 (13)
C130.5485 (3)0.7048 (6)0.64667 (18)0.0405 (13)
C140.5122 (2)0.7806 (6)0.67659 (18)0.0411 (13)
C150.5311 (2)0.7421 (6)0.72934 (19)0.0513 (14)
H150.56630.67190.74530.062*
C160.4966 (3)0.8096 (6)0.7584 (2)0.0570 (15)
H160.50870.78000.79370.068*
C170.4303 (2)0.9544 (6)0.6870 (2)0.0531 (15)
H170.39631.02890.67210.064*
C180.4614 (2)0.8892 (6)0.65543 (19)0.0475 (14)
H180.44790.91890.62010.057*
C190.7020 (3)0.2939 (6)0.3780 (2)0.0560 (15)
H190.66550.24320.38120.067*
C200.7083 (3)0.2884 (7)0.3291 (2)0.0684 (18)
H200.67640.23790.30040.082*
C210.7624 (3)0.3590 (7)0.32447 (19)0.0704 (18)
H210.76850.35390.29250.084*
C220.8081 (3)0.4382 (6)0.36705 (19)0.0450 (14)
C230.7967 (2)0.4395 (5)0.41476 (18)0.0361 (12)
C240.8437 (2)0.5203 (5)0.46088 (18)0.0347 (12)
C250.9006 (2)0.5974 (5)0.45968 (19)0.0366 (12)
C260.8698 (3)0.5916 (6)0.5475 (2)0.0563 (16)
H260.86010.58960.57790.068*
C270.9269 (3)0.6722 (6)0.54986 (19)0.0594 (16)
H270.95390.72350.58070.071*
C280.9424 (2)0.6740 (6)0.50568 (19)0.0545 (15)
H280.98050.72600.50620.065*
C290.9102 (2)0.5912 (6)0.41070 (19)0.0389 (13)
C300.8663 (3)0.5148 (6)0.36690 (19)0.0453 (14)
C310.9408 (3)0.6143 (6)0.3431 (2)0.0475 (14)
C320.9772 (3)0.6646 (6)0.3097 (2)0.0489 (14)
C330.9535 (3)0.6121 (6)0.2575 (2)0.0639 (17)
H330.91620.54630.24470.077*
C340.9863 (3)0.6595 (7)0.2252 (2)0.0756 (19)
H340.97100.62100.19070.091*
C351.0604 (3)0.8106 (6)0.2904 (2)0.0579 (15)
H351.09670.88000.30140.070*
C361.0314 (3)0.7674 (6)0.3266 (2)0.0561 (15)
H361.04810.80670.36100.067*
C370.6338 (3)0.1061 (6)0.50156 (19)0.0403 (13)
C380.6636 (2)0.0379 (5)0.55716 (18)0.0349 (12)
C390.7235 (2)0.0407 (5)0.57444 (18)0.0434 (13)
H390.74680.05350.55220.052*
C400.7486 (2)0.1003 (5)0.6254 (2)0.0423 (13)
C410.7181 (3)0.0741 (5)0.66075 (19)0.0472 (14)
H410.73610.11550.69490.057*
C420.6608 (2)0.0137 (6)0.64488 (19)0.0407 (13)
C430.6323 (2)0.0650 (5)0.59284 (17)0.0351 (12)
H430.59170.11820.58150.042*
C440.8736 (3)0.1424 (6)0.5129 (2)0.0470 (14)
C450.8530 (2)0.0571 (6)0.4602 (2)0.0439 (14)
C460.7958 (2)0.0331 (6)0.4413 (2)0.0482 (14)
H460.76970.04550.46140.058*
C470.8125 (3)0.0839 (6)0.3595 (2)0.0495 (14)
H470.79850.13120.32620.059*
C480.7772 (3)0.1052 (6)0.3921 (2)0.0477 (14)
C490.8687 (3)0.0087 (6)0.3778 (2)0.0494 (14)
C500.8901 (2)0.0752 (6)0.42842 (19)0.0470 (14)
H500.92970.13250.44120.056*
C510.6322 (3)0.0621 (6)0.6850 (2)0.0479 (14)
C520.9079 (3)0.0441 (7)0.3441 (2)0.0551 (16)
N10.65586 (18)0.5075 (4)0.48869 (15)0.0378 (10)
N20.74218 (19)0.3867 (4)0.58012 (14)0.0347 (10)
N30.6016 (2)0.6158 (5)0.66824 (14)0.0434 (11)
N40.53191 (18)0.7276 (4)0.59346 (14)0.0393 (10)
H4A0.49890.78200.57250.047*
N50.4470 (2)0.9149 (5)0.73788 (16)0.0523 (12)
N60.74414 (19)0.3661 (5)0.41993 (15)0.0408 (10)
N70.82803 (19)0.5173 (5)0.50504 (15)0.0428 (11)
N80.8854 (2)0.5313 (5)0.32436 (15)0.0537 (12)
N90.95818 (18)0.6546 (4)0.39486 (15)0.0455 (11)
H7A0.99240.70900.41390.055*
N101.0382 (2)0.7566 (6)0.24085 (18)0.0602 (13)
N110.8121 (2)0.1868 (6)0.64354 (19)0.0646 (14)
N120.7165 (2)0.2004 (6)0.3723 (2)0.0667 (14)
O10.82859 (16)0.1734 (4)0.53061 (12)0.0502 (9)
O20.93284 (18)0.1821 (4)0.53423 (13)0.0639 (11)
O30.9592 (2)0.1171 (5)0.36019 (15)0.0900 (15)
O40.87938 (17)0.0072 (4)0.29559 (14)0.0705 (11)
H40.90270.01470.27880.106*
O50.57270 (17)0.1200 (4)0.48219 (12)0.0573 (10)
O60.67361 (16)0.1446 (3)0.47948 (11)0.0446 (9)
O70.58037 (18)0.1549 (4)0.66617 (13)0.0674 (11)
H9A0.56690.17730.68970.101*
O80.65787 (18)0.0239 (5)0.73147 (14)0.0726 (12)
O90.8533 (2)0.1451 (6)0.62548 (17)0.1025 (16)
O100.8222 (2)0.2911 (5)0.67712 (18)0.1011 (16)
O110.6839 (2)0.2126 (5)0.39982 (18)0.1066 (16)
O120.6987 (2)0.2588 (6)0.32858 (19)0.1047 (17)
Mn10.74582 (4)0.33502 (8)0.50134 (3)0.0390 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.033 (3)0.056 (3)0.039 (3)0.007 (3)0.011 (3)0.002 (3)
C20.047 (4)0.071 (4)0.033 (3)0.018 (3)0.011 (3)0.007 (3)
C30.053 (4)0.063 (4)0.034 (3)0.009 (3)0.019 (3)0.003 (3)
C40.040 (3)0.039 (3)0.033 (3)0.002 (3)0.014 (3)0.001 (3)
C50.032 (3)0.037 (3)0.036 (3)0.004 (3)0.016 (2)0.000 (2)
C60.033 (3)0.036 (3)0.035 (3)0.001 (3)0.016 (2)0.000 (2)
C70.052 (4)0.070 (4)0.044 (3)0.020 (3)0.021 (3)0.021 (3)
C80.037 (3)0.059 (4)0.050 (3)0.009 (3)0.019 (3)0.005 (3)
C90.060 (4)0.054 (4)0.033 (3)0.008 (3)0.021 (3)0.007 (3)
C100.034 (3)0.038 (3)0.034 (3)0.003 (3)0.013 (2)0.002 (3)
C110.029 (3)0.040 (3)0.036 (3)0.001 (3)0.013 (2)0.006 (3)
C120.038 (3)0.047 (3)0.032 (3)0.003 (3)0.014 (3)0.006 (3)
C130.048 (4)0.047 (3)0.032 (3)0.000 (3)0.021 (3)0.004 (3)
C140.034 (3)0.051 (3)0.039 (3)0.003 (3)0.015 (3)0.007 (3)
C150.050 (4)0.068 (4)0.039 (3)0.011 (3)0.021 (3)0.002 (3)
C160.056 (4)0.076 (4)0.043 (3)0.001 (4)0.024 (3)0.001 (3)
C170.038 (4)0.067 (4)0.059 (4)0.003 (3)0.023 (3)0.004 (3)
C180.042 (4)0.058 (4)0.047 (3)0.005 (3)0.021 (3)0.010 (3)
C190.047 (4)0.070 (4)0.054 (4)0.013 (3)0.023 (3)0.004 (3)
C200.061 (4)0.099 (5)0.040 (4)0.031 (4)0.013 (3)0.012 (3)
C210.075 (5)0.108 (5)0.032 (3)0.030 (4)0.026 (3)0.006 (3)
C220.047 (4)0.056 (4)0.036 (3)0.008 (3)0.019 (3)0.003 (3)
C230.028 (3)0.048 (3)0.034 (3)0.000 (3)0.013 (2)0.004 (3)
C240.029 (3)0.038 (3)0.039 (3)0.004 (3)0.015 (2)0.008 (3)
C250.031 (3)0.038 (3)0.043 (3)0.002 (3)0.016 (3)0.006 (3)
C260.054 (4)0.078 (4)0.046 (4)0.017 (3)0.028 (3)0.009 (3)
C270.058 (4)0.079 (4)0.042 (3)0.025 (4)0.019 (3)0.013 (3)
C280.040 (3)0.069 (4)0.055 (4)0.019 (3)0.018 (3)0.001 (3)
C290.034 (3)0.051 (3)0.041 (3)0.001 (3)0.024 (3)0.010 (3)
C300.045 (4)0.059 (4)0.039 (3)0.005 (3)0.022 (3)0.006 (3)
C310.051 (4)0.058 (4)0.044 (4)0.005 (3)0.028 (3)0.009 (3)
C320.046 (4)0.063 (4)0.048 (4)0.008 (3)0.028 (3)0.019 (3)
C330.076 (5)0.073 (4)0.057 (4)0.014 (3)0.041 (4)0.000 (3)
C340.098 (6)0.081 (5)0.068 (4)0.012 (4)0.055 (4)0.001 (4)
C350.039 (3)0.079 (4)0.058 (4)0.003 (3)0.021 (3)0.015 (4)
C360.043 (4)0.083 (4)0.048 (3)0.007 (3)0.024 (3)0.018 (3)
C370.043 (4)0.039 (3)0.043 (3)0.004 (3)0.021 (3)0.001 (3)
C380.028 (3)0.039 (3)0.038 (3)0.000 (3)0.013 (2)0.001 (2)
C390.040 (3)0.055 (4)0.039 (3)0.000 (3)0.019 (3)0.008 (3)
C400.035 (3)0.041 (3)0.053 (4)0.007 (3)0.019 (3)0.002 (3)
C410.052 (4)0.044 (3)0.042 (3)0.007 (3)0.013 (3)0.002 (3)
C420.040 (3)0.046 (3)0.039 (3)0.003 (3)0.019 (3)0.002 (3)
C430.027 (3)0.041 (3)0.041 (3)0.002 (2)0.016 (2)0.001 (3)
C440.040 (4)0.052 (4)0.051 (4)0.008 (3)0.020 (3)0.011 (3)
C450.032 (3)0.046 (3)0.058 (4)0.005 (3)0.022 (3)0.006 (3)
C460.045 (4)0.051 (4)0.055 (4)0.011 (3)0.026 (3)0.011 (3)
C470.044 (4)0.054 (4)0.054 (4)0.000 (3)0.023 (3)0.001 (3)
C480.031 (3)0.046 (3)0.064 (4)0.006 (3)0.015 (3)0.004 (3)
C490.051 (4)0.054 (4)0.050 (4)0.005 (3)0.027 (3)0.002 (3)
C500.032 (3)0.059 (4)0.052 (4)0.005 (3)0.019 (3)0.001 (3)
C510.049 (4)0.057 (4)0.044 (4)0.005 (3)0.024 (3)0.006 (3)
C520.054 (4)0.067 (4)0.048 (4)0.006 (3)0.023 (3)0.003 (3)
N10.038 (3)0.046 (3)0.034 (2)0.002 (2)0.019 (2)0.003 (2)
N20.029 (2)0.043 (3)0.032 (2)0.001 (2)0.0108 (19)0.001 (2)
N30.039 (3)0.055 (3)0.039 (3)0.007 (2)0.019 (2)0.006 (2)
N40.038 (3)0.045 (3)0.038 (3)0.007 (2)0.018 (2)0.001 (2)
N50.048 (3)0.069 (3)0.042 (3)0.003 (3)0.020 (2)0.012 (3)
N60.027 (2)0.052 (3)0.042 (3)0.009 (2)0.011 (2)0.003 (2)
N70.043 (3)0.053 (3)0.038 (3)0.006 (2)0.023 (2)0.003 (2)
N80.050 (3)0.077 (3)0.041 (3)0.010 (3)0.025 (2)0.004 (2)
N90.036 (3)0.060 (3)0.046 (3)0.005 (2)0.022 (2)0.005 (2)
N100.056 (3)0.075 (4)0.060 (3)0.007 (3)0.034 (3)0.016 (3)
N110.054 (4)0.074 (4)0.060 (4)0.011 (3)0.014 (3)0.009 (3)
N120.050 (4)0.064 (4)0.088 (4)0.003 (3)0.028 (3)0.008 (3)
O10.044 (2)0.063 (2)0.054 (2)0.011 (2)0.0301 (18)0.0069 (19)
O20.046 (3)0.093 (3)0.058 (2)0.007 (2)0.027 (2)0.009 (2)
O30.073 (3)0.145 (4)0.066 (3)0.048 (3)0.042 (2)0.026 (3)
O40.070 (3)0.102 (3)0.050 (2)0.022 (3)0.034 (2)0.012 (2)
O50.038 (2)0.088 (3)0.048 (2)0.011 (2)0.0190 (18)0.016 (2)
O60.050 (2)0.052 (2)0.040 (2)0.0106 (19)0.0256 (17)0.0011 (17)
O70.065 (3)0.093 (3)0.060 (2)0.021 (3)0.041 (2)0.000 (2)
O80.078 (3)0.106 (3)0.039 (2)0.004 (3)0.028 (2)0.000 (2)
O90.065 (3)0.146 (4)0.107 (4)0.043 (3)0.044 (3)0.016 (3)
O100.075 (4)0.083 (3)0.119 (4)0.007 (3)0.005 (3)0.028 (3)
O110.079 (4)0.133 (4)0.120 (4)0.049 (3)0.052 (3)0.008 (3)
O120.069 (3)0.133 (4)0.108 (4)0.027 (3)0.028 (3)0.042 (3)
Mn10.0346 (5)0.0506 (5)0.0381 (4)0.0011 (4)0.0207 (3)0.0009 (4)
Geometric parameters (Å, º) top
C1—N21.327 (5)C30—N81.378 (5)
C1—C21.401 (5)C31—N81.313 (6)
C1—H10.9300C31—N91.359 (5)
C2—C31.363 (6)C31—C321.473 (6)
C2—H20.9300C32—C361.384 (6)
C3—C41.391 (6)C32—C331.390 (6)
C3—H30.9300C33—C341.381 (6)
C4—C51.401 (5)C33—H330.9300
C4—C121.421 (6)C34—N101.320 (6)
C5—N21.361 (5)C34—H340.9300
C5—C61.451 (6)C35—N101.330 (6)
C6—N11.358 (5)C35—C361.400 (6)
C6—C101.410 (6)C35—H350.9300
C7—C81.358 (6)C36—H360.9300
C7—C91.385 (6)C37—O51.242 (5)
C7—H70.9300C37—O61.266 (5)
C8—C101.391 (6)C37—C381.518 (6)
C8—H80.9300C38—C391.374 (6)
C9—N11.321 (5)C38—C431.398 (5)
C9—H90.9300C39—C401.380 (6)
C10—C111.430 (6)C39—H390.9300
C11—N41.373 (5)C40—C411.377 (6)
C11—C121.388 (6)C40—N111.469 (6)
C12—N31.367 (5)C41—C421.366 (6)
C13—N31.311 (5)C41—H410.9300
C13—N41.372 (5)C42—C431.387 (6)
C13—C141.469 (6)C42—C511.500 (6)
C14—C181.371 (6)C43—H430.9300
C14—C151.378 (6)C44—O21.247 (5)
C15—C161.393 (6)C44—O11.269 (5)
C15—H150.9300C44—C451.510 (6)
C16—N51.335 (6)C45—C461.378 (6)
C16—H160.9300C45—C501.395 (6)
C17—N51.337 (5)C46—C481.382 (6)
C17—C181.386 (6)C46—H460.9300
C17—H170.9300C47—C491.369 (6)
C18—H180.9300C47—C481.385 (6)
C19—N61.313 (5)C47—H470.9300
C19—C201.390 (6)C48—N121.458 (6)
C19—H190.9300C49—C501.394 (6)
C20—C211.361 (7)C49—C521.499 (6)
C20—H200.9300C50—H500.9300
C21—C221.381 (6)C51—O81.221 (5)
C21—H210.9300C51—O71.300 (6)
C22—C231.413 (5)C52—O31.199 (6)
C22—C301.416 (6)C52—O41.305 (6)
C23—N61.347 (5)Mn1—O12.142 (3)
C23—C241.455 (6)Mn1—O62.142 (3)
C24—N71.368 (5)Mn1—N12.339 (4)
C24—C251.404 (6)Mn1—N22.220 (3)
C25—C281.397 (6)Mn1—N62.221 (4)
C25—C291.428 (6)Mn1—N72.309 (4)
C26—N71.326 (5)N4—H4A0.8600
C26—C271.391 (6)N9—H7A0.8600
C26—H260.9300N11—O101.214 (5)
C27—C281.366 (6)N11—O91.222 (5)
C27—H270.9300N12—O121.208 (5)
C28—H280.9300N12—O111.214 (5)
C29—N91.373 (5)O4—H40.8200
C29—C301.375 (6)O7—H9A0.8200
N2—C1—C2123.2 (4)N10—C35—C36122.8 (5)
N2—C1—H1118.4N10—C35—H35118.6
C2—C1—H1118.4C36—C35—H35118.6
C3—C2—C1118.5 (4)C32—C36—C35118.2 (5)
C3—C2—H2120.7C32—C36—H36120.9
C1—C2—H2120.7C35—C36—H36120.9
C2—C3—C4120.1 (5)O5—C37—O6126.2 (5)
C2—C3—H3119.9O5—C37—C38116.9 (4)
C4—C3—H3119.9O6—C37—C38116.9 (5)
C3—C4—C5117.9 (5)C39—C38—C43118.9 (4)
C3—C4—C12123.7 (4)C39—C38—C37121.1 (4)
C5—C4—C12118.3 (4)C43—C38—C37119.9 (4)
N2—C5—C4122.2 (4)C38—C39—C40118.9 (4)
N2—C5—C6117.5 (4)C38—C39—H39120.5
C4—C5—C6120.3 (4)C40—C39—H39120.5
N1—C6—C10121.4 (4)C41—C40—C39122.4 (5)
N1—C6—C5117.0 (4)C41—C40—N11118.6 (5)
C10—C6—C5121.6 (4)C39—C40—N11118.9 (5)
C8—C7—C9119.2 (5)C42—C41—C40118.9 (5)
C8—C7—H7120.4C42—C41—H41120.6
C9—C7—H7120.4C40—C41—H41120.6
C7—C8—C10119.0 (5)C41—C42—C43119.7 (4)
C7—C8—H8120.5C41—C42—C51119.2 (5)
C10—C8—H8120.5C43—C42—C51121.1 (5)
N1—C9—C7124.0 (5)C42—C43—C38121.0 (5)
N1—C9—H9118.0C42—C43—H43119.5
C7—C9—H9118.0C38—C43—H43119.5
C8—C10—C6118.7 (4)O2—C44—O1125.7 (5)
C8—C10—C11125.5 (5)O2—C44—C45117.1 (5)
C6—C10—C11115.9 (4)O1—C44—C45117.2 (5)
N4—C11—C12105.2 (4)C46—C45—C50118.5 (5)
N4—C11—C10131.6 (4)C46—C45—C44121.0 (5)
C12—C11—C10123.2 (4)C50—C45—C44120.5 (5)
N3—C12—C11111.1 (4)C45—C46—C48119.6 (5)
N3—C12—C4128.3 (5)C45—C46—H46120.2
C11—C12—C4120.6 (4)C48—C46—H46120.2
N3—C13—N4113.2 (4)C49—C47—C48118.1 (5)
N3—C13—C14123.8 (4)C49—C47—H47121.0
N4—C13—C14123.0 (5)C48—C47—H47121.0
C18—C14—C15118.1 (4)C46—C48—C47122.4 (5)
C18—C14—C13124.0 (4)C46—C48—N12119.3 (5)
C15—C14—C13117.9 (5)C47—C48—N12118.2 (5)
C14—C15—C16119.2 (5)C47—C49—C50120.3 (5)
C14—C15—H15120.4C47—C49—C52121.4 (5)
C16—C15—H15120.4C50—C49—C52118.3 (5)
N5—C16—C15122.8 (5)C49—C50—C45121.0 (5)
N5—C16—H16118.6C49—C50—H50119.5
C15—C16—H16118.6C45—C50—H50119.5
N5—C17—C18122.8 (5)O8—C51—O7123.9 (5)
N5—C17—H17118.6O8—C51—C42122.3 (5)
C18—C17—H17118.6O7—C51—C42113.7 (5)
C14—C18—C17119.7 (5)O3—C52—O4124.2 (5)
C14—C18—H18120.2O3—C52—C49122.6 (5)
C17—C18—H18120.2O4—C52—C49113.2 (5)
N6—C19—C20124.4 (5)C9—N1—C6117.7 (4)
N6—C19—H19117.8C9—N1—Mn1127.4 (3)
C20—C19—H19117.8C6—N1—Mn1114.4 (3)
C21—C20—C19118.1 (5)C1—N2—C5118.0 (4)
C21—C20—H20120.9C1—N2—Mn1123.3 (3)
C19—C20—H20120.9C5—N2—Mn1118.0 (3)
C20—C21—C22120.2 (5)C13—N3—C12104.5 (4)
C20—C21—H21119.9C13—N4—C11106.1 (4)
C22—C21—H21119.9C13—N4—H4A126.9
C21—C22—C23117.3 (5)C11—N4—H4A126.9
C21—C22—C30125.1 (5)C16—N5—C17117.4 (4)
C23—C22—C30117.6 (5)C19—N6—C23117.3 (4)
N6—C23—C22122.7 (4)C19—N6—Mn1124.5 (3)
N6—C23—C24117.9 (4)C23—N6—Mn1117.2 (3)
C22—C23—C24119.4 (4)C26—N7—C24116.4 (4)
N7—C24—C25122.6 (4)C26—N7—Mn1127.4 (3)
N7—C24—C23115.3 (4)C24—N7—Mn1114.6 (3)
C25—C24—C23122.1 (4)C31—N8—C30104.1 (4)
C28—C25—C24118.0 (4)C31—N9—C29106.4 (4)
C28—C25—C29125.7 (5)C31—N9—H7A126.8
C24—C25—C29116.3 (4)C29—N9—H7A126.8
N7—C26—C27125.0 (5)C34—N10—C35118.4 (5)
N7—C26—H26117.5O10—N11—O9123.2 (6)
C27—C26—H26117.5O10—N11—C40118.7 (5)
C28—C27—C26118.2 (5)O9—N11—C40118.0 (5)
C28—C27—H27120.9O12—N12—O11122.1 (6)
C26—C27—H27120.9O12—N12—C48119.6 (5)
C27—C28—C25119.7 (5)O11—N12—C48118.2 (6)
C27—C28—H28120.1C44—O1—Mn1130.2 (3)
C25—C28—H28120.1C52—O4—H4109.5
N9—C29—C30105.5 (4)C37—O6—Mn1127.8 (3)
N9—C29—C25132.3 (5)C51—O7—H9A109.5
C30—C29—C25122.2 (4)O6—Mn1—O194.61 (12)
C29—C30—N8110.8 (5)O6—Mn1—N297.07 (12)
C29—C30—C22122.5 (4)O1—Mn1—N294.91 (13)
N8—C30—C22126.6 (5)O6—Mn1—N693.88 (13)
N8—C31—N9113.2 (4)O1—Mn1—N698.23 (12)
N8—C31—C32122.2 (5)N2—Mn1—N6162.14 (13)
N9—C31—C32124.5 (5)O6—Mn1—N7164.73 (12)
C36—C32—C33118.5 (5)O1—Mn1—N781.61 (13)
C36—C32—C31123.7 (5)N2—Mn1—N797.99 (13)
C33—C32—C31117.6 (5)N6—Mn1—N772.19 (14)
C34—C33—C32118.8 (5)O6—Mn1—N185.01 (13)
C34—C33—H33120.6O1—Mn1—N1167.13 (12)
C32—C33—H33120.6N2—Mn1—N172.42 (13)
N10—C34—C33123.3 (6)N6—Mn1—N194.62 (13)
N10—C34—H34118.4N7—Mn1—N1101.96 (12)
C33—C34—H34118.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H9A···N10i0.821.812.629 (5)176
O4—H4···N5ii0.821.822.636 (5)173
N9—H7A···O2iii0.861.942.789 (5)171
N4—H4A···O5iv0.861.892.745 (5)171
Symmetry codes: (i) x1/2, y+1, z+1/2; (ii) x+1/2, y+1, z1/2; (iii) x+2, y+1, z+1; (iv) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Mn(C8H4NO6)2(C18H11N5)2]
Mr1069.82
Crystal system, space groupMonoclinic, P2/n
Temperature (K)293
a, b, c (Å)21.791 (3), 8.2215 (12), 27.270 (4)
β (°) 111.767 (3)
V3)4537.2 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.38
Crystal size (mm)0.22 × 0.18 × 0.16
Data collection
DiffractometerBruker APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.45, 0.69
No. of measured, independent and
observed [I > 2σ(I)] reflections
22806, 8037, 3602
Rint0.105
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.126, 0.95
No. of reflections8037
No. of parameters694
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.24

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006).

Selected geometric parameters (Å, º) top
Mn1—O12.142 (3)Mn1—N22.220 (3)
Mn1—O62.142 (3)Mn1—N62.221 (4)
Mn1—N12.339 (4)Mn1—N72.309 (4)
N6—Mn1—N772.19 (14)N2—Mn1—N172.42 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H9A···N10i0.821.812.629 (5)176
O4—H4···N5ii0.821.822.636 (5)173
N9—H7A···O2iii0.861.942.789 (5)171
N4—H4A···O5iv0.861.892.745 (5)171
Symmetry codes: (i) x1/2, y+1, z+1/2; (ii) x+1/2, y+1, z1/2; (iii) x+2, y+1, z+1; (iv) x+1, y+1, z+1.
 

Acknowledgements

The authors thank Jilin Normal University for supporting this work.

References

First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (1999). 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 citationWang, X. Y., Ma, X. Y., Liu, Y., Xu, Z. L. & Kong, Z. G. (2010). Chin. J. Inorg. Chem. 26, 1482–1484.  CAS Google Scholar

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