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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): m684–m685.
Published online 2010 May 22. doi:  10.1107/S1600536810017794
PMCID: PMC2979398

Bis[4-amino-N-(pyrimidin-2-yl)benzene­sulfonamidato](2,2′-bipyridine)manganese(II)

Abstract

The title compound, [Mn(C10H9N4O2S)2(C10H8N2)], contains a distorted octa­hedral [Mn(sdz)2(bpy)] (sdz is the sulfadiazine anion and bpy is 2,2′-bipyridine) complex mol­ecule. A three-dimensional network is generated by N—H(...)N, N—H(...)O and C—H(...)O hydrogen bonds from the sulfadiazine ligands.

Related literature

For mono-ligand sulfadiazine–metal complexes, see: Yuan et al. (2001 [triangle]); Wang et al. (2005 [triangle]). For mixed-ligand sulfadiazine–metal complexes, see: Ajibade et al. (2006 [triangle]); Brown et al. (1987 [triangle]); Hossain et al. (2006 [triangle]); Wang et al. (2009 [triangle], 2010 [triangle]). For 2,2′-bipyridine–Mn(II) complexes, see: Chen et al. (1995 [triangle]); Cheng et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m684-scheme1.jpg

Experimental

Crystal data

  • [Mn(C10H9N4O2S)2(C10H8N2)]
  • M r = 709.67
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m684-efi1.jpg
  • a = 20.121 (3) Å
  • b = 17.555 (3) Å
  • c = 17.956 (3) Å
  • β = 106.973 (4)°
  • V = 6066.4 (17) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.63 mm−1
  • T = 193 K
  • 0.25 × 0.17 × 0.15 mm

Data collection

  • Rigaku Mercury CCD diffractometer
  • Absorption correction: multi-scan (REQAB; Jacobson, 1998 [triangle]) T min = 0.859, T max = 0.912
  • 28490 measured reflections
  • 5533 independent reflections
  • 4438 reflections with I > 2σ(I)
  • R int = 0.077

Refinement

  • R[F 2 > 2σ(F 2)] = 0.073
  • wR(F 2) = 0.167
  • S = 1.17
  • 5533 reflections
  • 441 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.58 e Å−3

Data collection: CrystalClear (Rigaku, 1999 [triangle]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2000 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017794/hg2677sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017794/hg2677Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Guangxi Natural Science Foundation of China (No. 0991003, 2010GXNSFF013001) and the Open Foundation of the Key Laboratory for the Chemistry and Mol­ecular Engineering of Medicinal Resources (Ministry of Education of China) for financial support.

supplementary crystallographic information

Comment

In the title compound, [Mn(sdz)2(bpy)] (where sdz is the sulfadiazine anion and bpy is 2,2'-bipyridine), the Mn(II) ion has six-coordinated distorted octahedral geometry and contains two bidentate N-coordinated sulfadiazinate anions and one chelating 2,2'-bipyridine ligand. The coordination mode of sulfadiazine is similar to its cobalt(II) complex (Ajibade et al., 2006; Wang et al. 2010), nickel(II) complex (Wang et al.200 9), and copper(II) complex (Brown et al., 1987), but different from Zn(sdz)2 (Yuan et al., 2001), polymeric Cd(II) complex (Wang et al. 2005), and its copper complex (Hossain et al. 2006). The Mn—N bond distances involving the sulfonamide atoms N1, N5,the pyrimido atoms N2, N6, and the 2,2'-bipyridine atoms N9, N10, are very similar, at 2.242 (4), 2.234 (4), 2.312 (4), 2.278 (4), 2.235 (4), 2.225 (4) Å, respectively. The bond distances of the chelating bpy to Mn(II), Mn—N are consistent with those for the reported bpy-Mn(II) complexes, e.g. diazidobis(2,2'-bipyridine)manganese(II) (Mn—N 2.322 (3) Å)(Cheng et al., 2004) and tris(2,2'-bipyridine)manganese(II) perchlorate hemihydrate (Mn—N 2.214 (4)-2.294 (4) Å)(Chen et al., 1995). The tetrahedral coordination at S is distorted, also found in the neutral sulfadiazine molecule. A three dimensional network is generated via N—H···N, N—H···O, C—H···O hydrogen bonds from the sulfadiazine ligands of the complex.

Experimental

0.1 mmol Mn(CH3COO)2.4H2O, 0.2 mmol sulfadiazine, 0.1 mmol 2,2'-bipyridine, ethanol (1 ml), methanol (1 ml) and pyridine (0.1 ml) were placed in a Pyrex tube (ca 25 cm). The tube was frozen with liquid N2, evacuated under vacuum, sealed with a torch and heated at 353 K for three days to give yellow block-shaped crystals, with a yield of 70%.

Refinement

The carbon H atoms were treated as riding, with C—H distances of 0.95 Å ,and Uiso(H) = 1.2Ueq (C). The H atoms attached to the amino N atoms were located in an electron-density map and refined isotropically.

Figures

Fig. 1.
The molecular structure, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
A packing plot of the title compound view along [001]. Hydrogen bonds are shown in the dashed line, and the H atoms that are not involved in hydrogen bonding are omitted.

Crystal data

[Mn(C10H9N4O2S)2(C10H8N2)]F(000) = 2920
Mr = 709.67Dx = 1.554 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2ycCell parameters from 8748 reflections
a = 20.121 (3) Åθ = 3.1–25.3°
b = 17.555 (3) ŵ = 0.63 mm1
c = 17.956 (3) ÅT = 193 K
β = 106.973 (4)°Block, yellow
V = 6066.4 (17) Å30.25 × 0.17 × 0.15 mm
Z = 8

Data collection

Rigaku Mercury CCD diffractometer5533 independent reflections
Radiation source: fine-focus sealed tube4438 reflections with I > 2σ(I)
graphiteRint = 0.077
Detector resolution: 7.31 pixels mm-1θmax = 25.3°, θmin = 3.1°
ω scansh = −24→24
Absorption correction: multi-scan (REQAB; Jacobson, 1998)k = −21→21
Tmin = 0.859, Tmax = 0.912l = −19→21
28490 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H atoms treated by a mixture of independent and constrained refinement
S = 1.17w = 1/[σ2(Fo2) + (0.0668P)2 + 12.6903P] where P = (Fo2 + 2Fc2)/3
5533 reflections(Δ/σ)max < 0.001
441 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = −0.58 e Å3

Special details

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)

xyzUiso*/Ueq
Mn10.68247 (3)0.52337 (4)0.53748 (4)0.0286 (2)
S10.85240 (6)0.60913 (7)0.57746 (7)0.0328 (3)
S20.66371 (6)0.37074 (6)0.39626 (7)0.0293 (3)
O10.81279 (17)0.67735 (18)0.5490 (2)0.0428 (9)
O20.90959 (17)0.6182 (2)0.6479 (2)0.0441 (9)
O30.66571 (17)0.32382 (17)0.46238 (18)0.0364 (8)
O40.60548 (15)0.36038 (18)0.32761 (19)0.0355 (8)
N10.79647 (18)0.5472 (2)0.5858 (2)0.0303 (9)
N20.75742 (18)0.4341 (2)0.6121 (2)0.0304 (9)
N30.8801 (2)0.4501 (2)0.6411 (2)0.0386 (10)
N40.9673 (3)0.5174 (3)0.3230 (3)0.0417 (11)
N50.66857 (19)0.45691 (19)0.4279 (2)0.0280 (8)
N60.67347 (17)0.5838 (2)0.4227 (2)0.0284 (8)
N70.6663 (2)0.5141 (2)0.3060 (2)0.0327 (9)
N80.9195 (2)0.3105 (3)0.3033 (3)0.0414 (11)
N90.59065 (18)0.4786 (2)0.5698 (2)0.0316 (9)
N100.63904 (19)0.6209 (2)0.5872 (2)0.0315 (9)
C10.8146 (2)0.4764 (2)0.6150 (3)0.0283 (10)
C20.7671 (3)0.3623 (3)0.6383 (3)0.0374 (11)
H20.72790.33130.63620.045*
C30.8325 (3)0.3328 (3)0.6680 (3)0.0422 (12)
H30.83950.28240.68810.051*
C40.8875 (3)0.3790 (3)0.6675 (3)0.0432 (13)
H40.93320.35900.68700.052*
C50.8884 (2)0.5770 (2)0.5047 (3)0.0290 (10)
C60.9558 (2)0.5958 (3)0.5071 (3)0.0333 (11)
H60.98450.62210.55100.040*
C70.9814 (2)0.5768 (3)0.4471 (3)0.0344 (11)
H71.02770.59060.44960.041*
C80.9409 (2)0.5373 (3)0.3821 (3)0.0314 (10)
C90.8722 (2)0.5200 (3)0.3791 (3)0.0344 (11)
H90.84290.49500.33470.041*
C100.8469 (2)0.5389 (3)0.4396 (3)0.0378 (12)
H100.80050.52580.43720.045*
C110.6687 (2)0.5180 (2)0.3812 (3)0.0280 (10)
C120.6778 (2)0.6488 (3)0.3868 (3)0.0388 (12)
H120.68130.69550.41440.047*
C130.6774 (3)0.6497 (3)0.3098 (3)0.0453 (13)
H130.68110.69600.28390.054*
C140.6713 (3)0.5814 (3)0.2727 (3)0.0401 (12)
H140.67070.58140.21950.048*
C150.7400 (2)0.3524 (2)0.3695 (3)0.0293 (10)
C160.8007 (2)0.3292 (3)0.4249 (3)0.0334 (11)
H160.80120.32290.47770.040*
C170.8598 (2)0.3153 (2)0.4036 (3)0.0308 (10)
H170.90090.29940.44180.037*
C180.8604 (2)0.3243 (2)0.3260 (3)0.0311 (10)
C190.7986 (2)0.3457 (2)0.2706 (3)0.0324 (10)
H190.79760.35050.21760.039*
C200.7388 (2)0.3599 (2)0.2918 (3)0.0310 (10)
H200.69720.37470.25360.037*
C210.5717 (3)0.4048 (3)0.5639 (3)0.0402 (12)
H210.59160.37140.53470.048*
C220.5244 (3)0.3759 (3)0.5988 (3)0.0426 (12)
H220.51210.32350.59350.051*
C230.4952 (3)0.4237 (3)0.6412 (3)0.0426 (12)
H230.46340.40450.66670.051*
C240.5127 (2)0.5001 (3)0.6465 (3)0.0350 (11)
H240.49240.53440.67460.042*
C250.5604 (2)0.5258 (3)0.6099 (3)0.0292 (10)
C260.6618 (2)0.6924 (3)0.5882 (3)0.0348 (11)
H260.70130.70210.57080.042*
C270.6300 (3)0.7526 (3)0.6135 (3)0.0398 (12)
H270.64750.80290.61330.048*
C280.5731 (3)0.7392 (3)0.6389 (3)0.0425 (12)
H280.55060.78000.65660.051*
C290.5491 (2)0.6656 (3)0.6382 (3)0.0381 (12)
H290.50960.65520.65540.046*
C300.5827 (2)0.6070 (3)0.6125 (3)0.0304 (10)
H4A1.009 (3)0.512 (3)0.330 (3)0.039 (15)*
H4B0.943 (3)0.485 (3)0.286 (3)0.042 (15)*
H8A0.962 (3)0.319 (3)0.336 (4)0.065 (19)*
H8B0.922 (3)0.323 (3)0.258 (3)0.051 (17)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn10.0292 (4)0.0308 (4)0.0283 (4)0.0005 (3)0.0123 (3)−0.0015 (3)
S10.0325 (6)0.0312 (6)0.0383 (7)−0.0039 (5)0.0159 (5)−0.0080 (5)
S20.0351 (6)0.0248 (6)0.0311 (6)−0.0019 (5)0.0143 (5)−0.0008 (5)
O10.0468 (19)0.0261 (17)0.065 (2)−0.0001 (15)0.0307 (18)−0.0028 (16)
O20.0404 (19)0.054 (2)0.039 (2)−0.0082 (16)0.0144 (16)−0.0165 (16)
O30.0485 (19)0.0284 (17)0.0398 (19)0.0005 (15)0.0247 (16)0.0037 (14)
O40.0298 (16)0.0360 (18)0.0414 (19)−0.0066 (14)0.0114 (15)−0.0060 (15)
N10.0296 (19)0.029 (2)0.035 (2)−0.0042 (16)0.0128 (17)−0.0001 (16)
N20.0296 (19)0.031 (2)0.032 (2)−0.0076 (17)0.0123 (17)−0.0053 (16)
N30.034 (2)0.037 (2)0.043 (2)0.0035 (19)0.0091 (19)0.0048 (19)
N40.033 (2)0.060 (3)0.035 (3)0.003 (2)0.015 (2)−0.005 (2)
N50.037 (2)0.0215 (19)0.026 (2)0.0002 (16)0.0103 (17)−0.0018 (15)
N60.0255 (19)0.0230 (19)0.036 (2)−0.0010 (15)0.0078 (17)0.0000 (16)
N70.040 (2)0.032 (2)0.028 (2)−0.0010 (18)0.0122 (18)0.0025 (16)
N80.035 (2)0.053 (3)0.040 (3)−0.003 (2)0.017 (2)−0.005 (2)
N90.0280 (19)0.037 (2)0.030 (2)0.0054 (17)0.0094 (17)0.0017 (17)
N100.031 (2)0.034 (2)0.031 (2)0.0008 (17)0.0123 (17)−0.0013 (16)
C10.031 (2)0.030 (2)0.027 (2)−0.003 (2)0.014 (2)−0.0031 (19)
C20.046 (3)0.036 (3)0.033 (3)−0.004 (2)0.016 (2)−0.003 (2)
C30.046 (3)0.034 (3)0.044 (3)0.005 (2)0.008 (2)0.001 (2)
C40.037 (3)0.043 (3)0.044 (3)0.008 (2)0.003 (2)0.000 (2)
C50.030 (2)0.025 (2)0.033 (3)−0.0008 (19)0.012 (2)0.0013 (19)
C60.030 (2)0.038 (3)0.034 (3)−0.004 (2)0.013 (2)−0.002 (2)
C70.025 (2)0.043 (3)0.038 (3)−0.002 (2)0.013 (2)0.002 (2)
C80.036 (3)0.031 (2)0.031 (3)0.005 (2)0.015 (2)0.0061 (19)
C90.030 (2)0.038 (3)0.034 (3)−0.002 (2)0.008 (2)−0.007 (2)
C100.034 (3)0.040 (3)0.042 (3)−0.004 (2)0.015 (2)−0.008 (2)
C110.031 (2)0.022 (2)0.029 (2)−0.0001 (19)0.007 (2)0.0000 (18)
C120.043 (3)0.025 (3)0.049 (3)−0.002 (2)0.014 (2)0.003 (2)
C130.060 (3)0.032 (3)0.042 (3)−0.004 (3)0.013 (3)0.011 (2)
C140.050 (3)0.040 (3)0.033 (3)−0.005 (2)0.016 (2)0.008 (2)
C150.036 (2)0.023 (2)0.030 (2)−0.001 (2)0.012 (2)−0.0006 (18)
C160.042 (3)0.029 (2)0.030 (3)−0.003 (2)0.013 (2)−0.004 (2)
C170.031 (2)0.031 (2)0.029 (2)−0.003 (2)0.006 (2)0.0013 (19)
C180.037 (3)0.023 (2)0.033 (3)−0.003 (2)0.011 (2)−0.0049 (19)
C190.045 (3)0.030 (2)0.025 (2)−0.001 (2)0.014 (2)−0.0019 (19)
C200.034 (2)0.030 (2)0.029 (3)−0.001 (2)0.009 (2)0.0005 (19)
C210.044 (3)0.031 (3)0.049 (3)0.003 (2)0.019 (3)−0.002 (2)
C220.043 (3)0.035 (3)0.054 (3)−0.004 (2)0.020 (3)0.001 (2)
C230.034 (3)0.050 (3)0.044 (3)0.001 (2)0.013 (2)0.009 (2)
C240.032 (2)0.044 (3)0.031 (3)0.007 (2)0.014 (2)0.005 (2)
C250.026 (2)0.034 (3)0.028 (2)0.0003 (19)0.008 (2)0.0029 (19)
C260.038 (3)0.034 (3)0.033 (3)−0.006 (2)0.011 (2)0.001 (2)
C270.045 (3)0.029 (3)0.048 (3)−0.001 (2)0.017 (3)−0.001 (2)
C280.044 (3)0.034 (3)0.053 (3)0.011 (2)0.020 (3)−0.001 (2)
C290.032 (2)0.044 (3)0.039 (3)0.007 (2)0.013 (2)−0.003 (2)
C300.029 (2)0.036 (3)0.025 (2)0.004 (2)0.0068 (19)−0.0015 (19)

Geometric parameters (Å, °)

Mn1—N102.225 (4)C6—C71.365 (6)
Mn1—N52.234 (4)C6—H60.9500
Mn1—N92.235 (4)C7—C81.396 (6)
Mn1—N12.242 (4)C7—H70.9500
Mn1—N62.278 (4)C8—C91.401 (6)
Mn1—N22.312 (4)C9—C101.367 (7)
S1—O11.447 (4)C9—H90.9500
S1—O21.449 (4)C10—H100.9500
S1—N11.603 (4)C12—C131.379 (7)
S1—C51.761 (4)C12—H120.9500
S2—O31.436 (3)C13—C141.360 (7)
S2—O41.443 (3)C13—H130.9500
S2—N51.609 (4)C14—H140.9500
S2—C151.766 (4)C15—C161.393 (6)
N1—C11.356 (6)C15—C201.395 (6)
N2—C21.339 (6)C16—C171.374 (6)
N2—C11.359 (5)C16—H160.9500
N3—C41.328 (6)C17—C181.405 (6)
N3—C11.344 (6)C17—H170.9500
N4—C81.364 (6)C18—C191.397 (6)
N4—H4A0.82 (5)C19—C201.388 (6)
N4—H4B0.89 (6)C19—H190.9500
N5—C111.361 (5)C20—H200.9500
N6—C121.326 (6)C21—C221.380 (7)
N6—C111.363 (5)C21—H210.9500
N7—C111.340 (6)C22—C231.376 (7)
N7—C141.341 (6)C22—H220.9500
N8—C181.387 (6)C23—C241.383 (7)
N8—H8A0.91 (6)C23—H230.9500
N8—H8B0.87 (6)C24—C251.387 (6)
N9—C211.345 (6)C24—H240.9500
N9—C251.354 (6)C25—C301.492 (6)
N10—C261.333 (6)C26—C271.379 (6)
N10—C301.360 (6)C26—H260.9500
C2—C31.369 (7)C27—C281.372 (7)
C2—H20.9500C27—H270.9500
C3—C41.375 (7)C28—C291.379 (7)
C3—H30.9500C28—H280.9500
C4—H40.9500C29—C301.383 (6)
C5—C61.383 (6)C29—H290.9500
C5—C101.395 (6)
N10—Mn1—N5142.44 (13)C6—C7—H7119.4
N10—Mn1—N973.45 (14)C8—C7—H7119.4
N5—Mn1—N998.33 (14)N4—C8—C7120.8 (4)
N10—Mn1—N1100.29 (14)N4—C8—C9121.2 (5)
N5—Mn1—N1106.80 (13)C7—C8—C9118.0 (4)
N9—Mn1—N1142.64 (14)C10—C9—C8120.6 (4)
N10—Mn1—N693.88 (13)C10—C9—H9119.7
N5—Mn1—N659.32 (13)C8—C9—H9119.7
N9—Mn1—N6123.06 (13)C9—C10—C5120.7 (4)
N1—Mn1—N693.76 (13)C9—C10—H10119.6
N10—Mn1—N2123.73 (13)C5—C10—H10119.6
N5—Mn1—N292.83 (13)N7—C11—N5125.1 (4)
N9—Mn1—N293.42 (13)N7—C11—N6124.8 (4)
N1—Mn1—N258.77 (13)N5—C11—N6110.1 (4)
N6—Mn1—N2134.94 (13)N6—C12—C13121.0 (5)
O1—S1—O2115.6 (2)N6—C12—H12119.5
O1—S1—N1105.4 (2)C13—C12—H12119.5
O2—S1—N1113.2 (2)C14—C13—C12117.1 (4)
O1—S1—C5107.9 (2)C14—C13—H13121.4
O2—S1—C5106.8 (2)C12—C13—H13121.4
N1—S1—C5107.7 (2)N7—C14—C13124.4 (5)
O3—S2—O4117.0 (2)N7—C14—H14117.8
O3—S2—N5105.28 (19)C13—C14—H14117.8
O4—S2—N5111.74 (19)C16—C15—C20119.9 (4)
O3—S2—C15107.7 (2)C16—C15—S2120.7 (3)
O4—S2—C15107.3 (2)C20—C15—S2119.5 (3)
N5—S2—C15107.4 (2)C17—C16—C15120.2 (4)
C1—N1—S1122.7 (3)C17—C16—H16119.9
C1—N1—Mn196.3 (3)C15—C16—H16119.9
S1—N1—Mn1139.2 (2)C16—C17—C18121.0 (4)
C2—N2—C1117.8 (4)C16—C17—H17119.5
C2—N2—Mn1147.7 (3)C18—C17—H17119.5
C1—N2—Mn193.1 (3)N8—C18—C19119.9 (4)
C4—N3—C1116.4 (4)N8—C18—C17121.9 (4)
C8—N4—H4A122 (4)C19—C18—C17118.2 (4)
C8—N4—H4B119 (3)C20—C19—C18121.1 (4)
H4A—N4—H4B111 (5)C20—C19—H19119.4
C11—N5—S2122.3 (3)C18—C19—H19119.4
C11—N5—Mn196.2 (3)C19—C20—C15119.6 (4)
S2—N5—Mn1141.3 (2)C19—C20—H20120.2
C12—N6—C11117.9 (4)C15—C20—H20120.2
C12—N6—Mn1147.3 (3)N9—C21—C22122.4 (4)
C11—N6—Mn194.2 (3)N9—C21—H21118.8
C11—N7—C14114.8 (4)C22—C21—H21118.8
C18—N8—H8A121 (4)C23—C22—C21119.3 (5)
C18—N8—H8B122 (4)C23—C22—H22120.4
H8A—N8—H8B106 (5)C21—C22—H22120.4
C21—N9—C25118.0 (4)C22—C23—C24119.2 (5)
C21—N9—Mn1123.7 (3)C22—C23—H23120.4
C25—N9—Mn1117.2 (3)C24—C23—H23120.4
C26—N10—C30118.8 (4)C23—C24—C25118.7 (4)
C26—N10—Mn1123.8 (3)C23—C24—H24120.6
C30—N10—Mn1117.3 (3)C25—C24—H24120.6
N3—C1—N1125.1 (4)N9—C25—C24122.3 (4)
N3—C1—N2124.0 (4)N9—C25—C30115.0 (4)
N1—C1—N2110.9 (4)C24—C25—C30122.7 (4)
N2—C2—C3121.2 (5)N10—C26—C27122.4 (4)
N2—C2—H2119.4N10—C26—H26118.8
C3—C2—H2119.4C27—C26—H26118.8
C2—C3—C4117.3 (5)C28—C27—C26119.3 (5)
C2—C3—H3121.4C28—C27—H27120.3
C4—C3—H3121.4C26—C27—H27120.3
N3—C4—C3123.3 (5)C27—C28—C29118.9 (5)
N3—C4—H4118.3C27—C28—H28120.6
C3—C4—H4118.3C29—C28—H28120.6
C6—C5—C10118.8 (4)C28—C29—C30119.7 (4)
C6—C5—S1120.9 (3)C28—C29—H29120.2
C10—C5—S1120.0 (3)C30—C29—H29120.2
C7—C6—C5120.7 (4)N10—C30—C29121.0 (4)
C7—C6—H6119.7N10—C30—C25115.8 (4)
C5—C6—H6119.7C29—C30—C25123.3 (4)
C6—C7—C8121.1 (4)
O1—S1—N1—C1−176.6 (3)C2—N2—C1—N1179.3 (4)
O2—S1—N1—C1−49.3 (4)Mn1—N2—C1—N19.4 (4)
C5—S1—N1—C168.5 (4)C1—N2—C2—C30.9 (7)
O1—S1—N1—Mn123.2 (4)Mn1—N2—C2—C3161.8 (4)
O2—S1—N1—Mn1150.4 (3)N2—C2—C3—C4−2.0 (7)
C5—S1—N1—Mn1−91.8 (3)C1—N3—C4—C30.8 (7)
N10—Mn1—N1—C1129.6 (3)C2—C3—C4—N31.1 (8)
N5—Mn1—N1—C1−76.7 (3)O1—S1—C5—C696.4 (4)
N9—Mn1—N1—C153.5 (4)O2—S1—C5—C6−28.5 (4)
N6—Mn1—N1—C1−135.7 (3)N1—S1—C5—C6−150.3 (4)
N2—Mn1—N1—C16.3 (2)O1—S1—C5—C10−77.0 (4)
N10—Mn1—N1—S1−67.0 (3)O2—S1—C5—C10158.2 (4)
N5—Mn1—N1—S186.7 (3)N1—S1—C5—C1036.3 (4)
N9—Mn1—N1—S1−143.2 (3)C10—C5—C6—C7−0.5 (7)
N6—Mn1—N1—S127.6 (3)S1—C5—C6—C7−174.0 (4)
N2—Mn1—N1—S1169.6 (4)C5—C6—C7—C8−0.6 (7)
N10—Mn1—N2—C2109.5 (6)C6—C7—C8—N4−178.9 (5)
N5—Mn1—N2—C2−61.4 (6)C6—C7—C8—C92.1 (7)
N9—Mn1—N2—C237.1 (6)N4—C8—C9—C10178.5 (5)
N1—Mn1—N2—C2−169.4 (6)C7—C8—C9—C10−2.4 (7)
N6—Mn1—N2—C2−109.1 (6)C8—C9—C10—C51.3 (7)
N10—Mn1—N2—C1−87.4 (3)C6—C5—C10—C90.2 (7)
N5—Mn1—N2—C1101.8 (3)S1—C5—C10—C9173.7 (4)
N9—Mn1—N2—C1−159.7 (3)C14—N7—C11—N5−176.1 (4)
N1—Mn1—N2—C1−6.2 (2)C14—N7—C11—N62.2 (7)
N6—Mn1—N2—C154.0 (3)S2—N5—C11—N7−1.3 (6)
O3—S2—N5—C11179.5 (3)Mn1—N5—C11—N7175.6 (4)
O4—S2—N5—C11−52.6 (4)S2—N5—C11—N6−179.8 (3)
C15—S2—N5—C1164.9 (4)Mn1—N5—C11—N6−2.9 (4)
O3—S2—N5—Mn14.3 (4)C12—N6—C11—N7−1.8 (6)
O4—S2—N5—Mn1132.3 (3)Mn1—N6—C11—N7−175.7 (4)
C15—S2—N5—Mn1−110.2 (3)C12—N6—C11—N5176.6 (4)
N10—Mn1—N5—C1151.9 (4)Mn1—N6—C11—N52.8 (4)
N9—Mn1—N5—C11125.5 (3)C11—N6—C12—C130.2 (7)
N1—Mn1—N5—C11−82.4 (3)Mn1—N6—C12—C13168.7 (4)
N6—Mn1—N5—C111.9 (2)N6—C12—C13—C140.8 (8)
N2—Mn1—N5—C11−140.6 (3)C11—N7—C14—C13−1.0 (7)
N10—Mn1—N5—S2−132.2 (3)C12—C13—C14—N7−0.4 (8)
N9—Mn1—N5—S2−58.6 (3)O3—S2—C15—C16−28.5 (4)
N1—Mn1—N5—S293.4 (3)O4—S2—C15—C16−155.2 (4)
N6—Mn1—N5—S2177.7 (4)N5—S2—C15—C1684.5 (4)
N2—Mn1—N5—S235.3 (3)O3—S2—C15—C20150.3 (3)
N10—Mn1—N6—C1236.2 (6)O4—S2—C15—C2023.5 (4)
N5—Mn1—N6—C12−171.7 (6)N5—S2—C15—C20−96.8 (4)
N9—Mn1—N6—C12108.9 (6)C20—C15—C16—C171.5 (7)
N1—Mn1—N6—C12−64.4 (6)S2—C15—C16—C17−179.8 (3)
N2—Mn1—N6—C12−112.5 (6)C15—C16—C17—C180.1 (7)
N10—Mn1—N6—C11−154.0 (3)C16—C17—C18—N8−179.9 (4)
N5—Mn1—N6—C11−1.9 (2)C16—C17—C18—C19−1.7 (6)
N9—Mn1—N6—C11−81.2 (3)N8—C18—C19—C20−179.9 (4)
N1—Mn1—N6—C11105.5 (3)C17—C18—C19—C201.9 (6)
N2—Mn1—N6—C1157.4 (3)C18—C19—C20—C15−0.4 (7)
N10—Mn1—N9—C21−175.6 (4)C16—C15—C20—C19−1.3 (6)
N5—Mn1—N9—C2142.0 (4)S2—C15—C20—C19179.9 (3)
N1—Mn1—N9—C21−90.3 (4)C25—N9—C21—C22−1.8 (7)
N6—Mn1—N9—C21100.6 (4)Mn1—N9—C21—C22166.2 (4)
N2—Mn1—N9—C21−51.4 (4)N9—C21—C22—C230.0 (8)
N10—Mn1—N9—C25−7.6 (3)C21—C22—C23—C241.6 (8)
N5—Mn1—N9—C25−150.0 (3)C22—C23—C24—C25−1.3 (7)
N1—Mn1—N9—C2577.7 (4)C21—N9—C25—C242.0 (6)
N6—Mn1—N9—C25−91.3 (3)Mn1—N9—C25—C24−166.8 (3)
N2—Mn1—N9—C25116.7 (3)C21—N9—C25—C30−178.7 (4)
N5—Mn1—N10—C26−91.8 (4)Mn1—N9—C25—C3012.5 (5)
N9—Mn1—N10—C26−173.9 (4)C23—C24—C25—N9−0.5 (7)
N1—Mn1—N10—C2644.1 (4)C23—C24—C25—C30−179.7 (4)
N6—Mn1—N10—C26−50.5 (4)C30—N10—C26—C27−0.3 (7)
N2—Mn1—N10—C26103.2 (4)Mn1—N10—C26—C27174.4 (4)
N5—Mn1—N10—C3083.0 (4)N10—C26—C27—C280.2 (7)
N9—Mn1—N10—C301.0 (3)C26—C27—C28—C29−0.2 (8)
N1—Mn1—N10—C30−141.1 (3)C27—C28—C29—C300.3 (8)
N6—Mn1—N10—C30124.4 (3)C26—N10—C30—C290.5 (6)
N2—Mn1—N10—C30−81.9 (3)Mn1—N10—C30—C29−174.6 (3)
C4—N3—C1—N1−179.9 (4)C26—N10—C30—C25−179.9 (4)
C4—N3—C1—N2−2.1 (7)Mn1—N10—C30—C255.0 (5)
S1—N1—C1—N31.1 (6)C28—C29—C30—N10−0.4 (7)
Mn1—N1—C1—N3168.3 (4)C28—C29—C30—C25179.9 (5)
S1—N1—C1—N2−176.9 (3)N9—C25—C30—N10−11.6 (6)
Mn1—N1—C1—N2−9.8 (4)C24—C25—C30—N10167.7 (4)
C2—N2—C1—N31.3 (7)N9—C25—C30—C29168.1 (4)
Mn1—N2—C1—N3−168.6 (4)C24—C25—C30—C29−12.6 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N8—H8B···O2i0.87 (6)2.17 (6)3.011 (6)163 (5)
N4—H4A···N3ii0.82 (5)2.23 (5)3.003 (6)156 (5)
C12—H12···O1iii0.952.323.248 (6)165

Symmetry codes: (i) x, −y+1, z−1/2; (ii) −x+2, −y+1, −z+1; (iii) −x+3/2, −y+3/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2677).

References

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