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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): m332–m333.
Published online 2010 February 24. doi:  10.1107/S1600536810006112
PMCID: PMC2983608

{2,2′-[3-Aza­pentane-1,5-diylbis(nitrilo­methyl­idyne)]dipyrrol-1-yl}(4-methyl­pyridine)cobalt(III) tetra­phenyl­borate

Abstract

The title compound, [Co(C14H17N5)(C6H7N)](C24H20B) or [Co{(pyrrole)2dien}(4-Mepy)]BPh4 where (pyrrole)2dien is 2,2′-[(3-aza­pentane-1,5-diylbis(nitrilo­methyl­idyne)]dipyrrole and 4-Mepy is 4-methyl­pyridine, contains a penta­dentate (pyrrole)2dien ligand furnishing an N5 set, such that two of the pyrrole N atoms and two of the dien N atoms occupy the equatorial positions while one of the imine N atoms of the (pyrrole)2dien ligand occupies the axial position. The 4-methyl­pyridine ligand occupies an axial position trans to one of the imine N atoms of the penta­dentate ligand. In the observed conformation of the penta­dentate ligand, the pyrrole rings attain asymmetrical positions owing to the structural demands. The geometry of the resulting CoN6 coordination can be described as distorted octa­hedral.

Related literature

For general background to the applications of transition metal–Schiff base complexes, see: Nishinaga & Tomita (1980 [triangle]); Speiser & Stahl (1995 [triangle]); Miodragović et al. (2006 [triangle]); Amirnasr et al. (2006 [triangle]); Morshedi et al. (2006 [triangle]); Meghdadi et al. (2007 [triangle], 2008 [triangle]); Park et al. (1998 [triangle]); Mishra et al. (2008 [triangle]). For the synthesis of the ligand, see: Kwiatkowski et al. (1993 [triangle]). For related structures, see: Meghdadi et al. (2007 [triangle], 2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m332-scheme1.jpg

Experimental

Crystal data

  • [Co(C14H17N5)(C6H7N)](C24H20B)
  • M r = 726.59
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m332-efi1.jpg
  • a = 11.0332 (16) Å
  • b = 19.559 (3) Å
  • c = 17.138 (3) Å
  • β = 92.164 (2)°
  • V = 3695.7 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.51 mm−1
  • T = 100 K
  • 0.52 × 0.46 × 0.35 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2003 [triangle]) T min = 0.71, T max = 0.84
  • 66110 measured reflections
  • 10797 independent reflections
  • 8767 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.104
  • S = 1.07
  • 10797 reflections
  • 474 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.57 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2003 [triangle]); cell refinement: SAINT (Bruker, 2003 [triangle]); data reduction: SAINT and XPREP (Bruker, 2003 [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 .

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810006112/dn2536sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006112/dn2536Isup2.hkl

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

Acknowledgments

Partial support of this work by the Isfahan University of Technology Research Council is gratefully acknowledged.

supplementary crystallographic information

Comment

Transition metal Schiff-base complexes have been extensively studied due to their applications, e.g., their ability to reversibly bind oxygen, and their use in catalysis for oxygenation and oxidation reactions of organic compounds (Nishinaga et al. 1980; Speiser et al., 1995; Park et al., 1998). Among these metal complexes, cobalt(III) Schiff base complexes with two amines in axial positions have attracted considerable interest due to their ability as antimicrobial agents (Miodragović et al., 2006; Mishra et al., 2008). Transition metal complexes with pentadentate ligands show interesting structural features and have also been playing an important role in the development of coordination chemistry (Amirnasr et al., 2006; Morshedi et al., 2006; Meghdadi et al., 2007; Meghdadi et al., 2008) . In this context, we herein report the synthesis and structure of the title compound, [Co{(pyrrole)2dien}(4-Mepy)]BPh4, (I), and make a brief comparison with reported structures.

The environment surrounding CoIII in (I) is distorted octahedral (Fig. 1), in which the three N atoms of the Schiff base ligand are arranged in facial positions. The geometric parameters are listed below in the supplementary materials. The two chelate bite angles (81.38 (5)°, 82.26 (5)°) formed by the two imine-N and the secondary amine-N of the Schiff base are similar. The five-membered chelate rings formed by the pyrrole-N and the imine-N atoms have almost identical bite angles (N1—Co1—N2 82.11 (5)°; N4—Co1—N5 82.22 (5)°). The three trans angles, (N2—Co1—N5 170.28 (5)°; N4—Co1—N6 170.80 (5)°, N1—Co1—N3 161.96 (5)°) deviate significantly from ideal. The Co—N(pyrrole), Co—N(imine), Co—N(secondary amine) and CoN-(4-methylpyridine) bond lengths are comparable with the bond lengths observed in related Co(III) complexes (Meghdadi et al., 2008). The conformation adopted by the (pyrrole)2dien in (I) is different from that of (Me-sal)2dpt in [Co{(Me-sal)2dpt}(py)]PF6 (Meghdadi et al., 2007). While the three donor N atoms of (Me-sal)2dpt occupy three meridional sites and the two phenolate-O atoms are trans to each other, the three N atoms of (pyrrole)2dien ligand are arranged in facial positions and the two pyrrole-N atoms are cis. This is presumably due to the structural demands imparted by (pyrrole)2dien Schiff base ligand which has forced the [Co{(pyrrole)2dien}(4-Mepy)]+ to attain such a twisted structure.

Experimental

The ligand was synthesized according to the literature (Kwiatkowski et al., 1993). To a stirring solution of Co(CH3COO)2.4H2O (0.249 g, 1 mmol) in absolute ethanol (50 ml) was added an equimolar amount of ligand (0.256 g, 1 mmol). The pink solution turned brown immediately upon the formation of Co(III) complex. To this solution was added dropwise 7.5 mmol of the 4-methylpyridine. The reaction mixture was stirred for about 4 h and then filtered off. To the brown filtrate was added NaBPh4 (0.342 g, 1 mmol). The solution was left undisturbed for three days. The brown microcrystalline product was filtered off and washed with cold methanol. Brown crystals of the compound suitable for X-ray crystallography were obtained by diffusion of diethyl ether in to the acetone solution of the product.

Refinement

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.95Å (aromatic), 0.99Å (methylene) and 0.98Å (methyl) with Uiso(H) = 1.2 Ueq(aromatic, methylene) or Uiso(H) = 1.5 Ueq(methyl). The N(3) bonded hydrogen H(3n) was freely refined.

Figures

Fig. 1.
Molecular view of [Co{(pyrrole)2dien}(4-Mepy)]+ , with the atom labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms omitted for clarity.

Crystal data

[Co(C14H17N5)(C6H7N)](C24H20B)F(000) = 1528
Mr = 726.59Dx = 1.306 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7791 reflections
a = 11.0332 (16) Åθ = 2.4–30.0°
b = 19.559 (3) ŵ = 0.51 mm1
c = 17.138 (3) ÅT = 100 K
β = 92.164 (2)°Prism, brown
V = 3695.7 (9) Å30.52 × 0.46 × 0.35 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer10797 independent reflections
Radiation source: normal-focus sealed tube8767 reflections with I > 2σ(I)
graphiteRint = 0.036
\ and ω scansθmax = 30.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2003)h = −15→15
Tmin = 0.71, Tmax = 0.84k = −27→27
66110 measured reflectionsl = −24→24

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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0519P)2 + 1.7914P] where P = (Fo2 + 2Fc2)/3
10797 reflections(Δ/σ)max = 0.002
474 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = −0.22 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
Co10.270495 (16)0.246611 (9)0.511104 (10)0.01323 (5)
N10.29289 (11)0.26519 (6)0.61977 (7)0.0168 (2)
N20.35020 (11)0.16303 (6)0.54069 (7)0.0169 (2)
N30.25046 (11)0.19607 (6)0.40752 (7)0.0168 (2)
H3N0.2513 (16)0.2203 (10)0.3655 (11)0.021 (4)*
N40.11170 (11)0.21273 (6)0.52448 (7)0.0174 (2)
N50.18479 (10)0.33239 (6)0.49985 (7)0.0168 (2)
N60.42291 (10)0.28990 (6)0.48320 (7)0.0149 (2)
C10.26993 (15)0.31506 (8)0.67082 (9)0.0243 (3)
H10.23250.35750.65800.029*
C20.30967 (17)0.29492 (9)0.74592 (10)0.0324 (4)
H20.30450.32120.79230.039*
C30.35806 (16)0.22953 (9)0.74040 (9)0.0281 (3)
H30.39210.20250.78170.034*
C40.34628 (13)0.21183 (7)0.66153 (8)0.0190 (3)
C50.37794 (13)0.15587 (7)0.61457 (8)0.0192 (3)
H50.41650.11610.63530.023*
C60.37524 (14)0.11217 (7)0.48109 (9)0.0208 (3)
H6A0.31900.07290.48450.025*
H6B0.45950.09520.48760.025*
C70.35670 (14)0.14869 (7)0.40325 (8)0.0204 (3)
H7A0.43050.17500.39140.024*
H7B0.34170.11480.36110.024*
C80.13076 (14)0.15881 (8)0.40369 (9)0.0218 (3)
H8A0.14040.11410.37750.026*
H8B0.07010.18590.37290.026*
C90.08666 (14)0.14765 (7)0.48620 (9)0.0216 (3)
H9A−0.00110.13710.48520.026*
H9B0.13180.11000.51280.026*
C100.02770 (13)0.25895 (7)0.53121 (9)0.0199 (3)
H10−0.05500.24760.53790.024*
C110.06867 (13)0.32712 (7)0.52786 (9)0.0192 (3)
C120.02430 (14)0.39236 (8)0.54421 (9)0.0240 (3)
H12−0.05280.40340.56360.029*
C130.11611 (15)0.43788 (8)0.52628 (10)0.0259 (3)
H130.11330.48620.53110.031*
C140.21353 (14)0.39927 (7)0.49984 (9)0.0209 (3)
H140.28860.41760.48420.025*
C150.43211 (13)0.31823 (7)0.41192 (8)0.0182 (3)
H150.36290.31780.37730.022*
C160.53711 (13)0.34777 (7)0.38701 (8)0.0206 (3)
H160.53960.36660.33600.025*
C170.63943 (13)0.34989 (8)0.43680 (9)0.0208 (3)
C180.62879 (13)0.32259 (8)0.51101 (9)0.0206 (3)
H180.69580.32420.54750.025*
C190.52091 (12)0.29305 (7)0.53198 (8)0.0177 (3)
H190.51590.27430.58290.021*
C200.75545 (15)0.38114 (10)0.41104 (11)0.0336 (4)
H20A0.76030.37650.35430.050*
H20B0.82440.35760.43680.050*
H20C0.75740.42970.42520.050*
B10.79035 (13)0.10736 (8)0.68052 (9)0.0149 (3)
C210.66500 (12)0.07260 (7)0.71036 (8)0.0168 (2)
C220.62423 (14)0.08440 (8)0.78607 (9)0.0240 (3)
H220.66630.11680.81830.029*
C230.52496 (15)0.05059 (9)0.81561 (10)0.0292 (3)
H230.50060.06010.86710.035*
C240.46146 (14)0.00298 (9)0.76998 (11)0.0292 (4)
H240.3943−0.02080.79010.035*
C250.49725 (13)−0.00932 (8)0.69501 (10)0.0251 (3)
H250.4538−0.04130.66300.030*
C260.59709 (13)0.02504 (7)0.66600 (9)0.0195 (3)
H260.61980.01580.61410.023*
C270.79551 (13)0.18974 (7)0.70191 (8)0.0169 (3)
C280.90322 (14)0.22802 (8)0.70670 (8)0.0207 (3)
H280.97850.20440.70610.025*
C290.90444 (16)0.29928 (8)0.71231 (9)0.0256 (3)
H290.97960.32310.71470.031*
C300.79626 (17)0.33553 (8)0.71446 (9)0.0278 (3)
H300.79660.38410.71680.033*
C310.68804 (16)0.29965 (8)0.71308 (9)0.0256 (3)
H310.61340.32350.71610.031*
C320.68832 (14)0.22831 (8)0.70729 (8)0.0208 (3)
H320.61290.20480.70700.025*
C330.79120 (11)0.10059 (7)0.58466 (8)0.0148 (2)
C340.73321 (13)0.14887 (7)0.53542 (8)0.0198 (3)
H340.69760.18790.55830.024*
C350.72561 (14)0.14192 (8)0.45425 (9)0.0230 (3)
H350.68560.17590.42310.028*
C360.77648 (13)0.08540 (8)0.41903 (8)0.0204 (3)
H360.77140.08020.36390.025*
C370.83468 (13)0.03682 (7)0.46558 (8)0.0190 (3)
H370.8704−0.00190.44220.023*
C380.84137 (12)0.04421 (7)0.54657 (8)0.0167 (2)
H380.88130.00990.57710.020*
C390.90644 (12)0.06510 (7)0.71932 (8)0.0167 (2)
C401.02475 (13)0.07448 (7)0.69319 (8)0.0191 (3)
H401.03670.10590.65190.023*
C411.12499 (13)0.03983 (8)0.72513 (9)0.0231 (3)
H411.20340.04850.70630.028*
C421.11045 (15)−0.00742 (8)0.78447 (11)0.0289 (3)
H421.1784−0.03140.80650.035*
C430.99522 (16)−0.01911 (8)0.81106 (11)0.0302 (4)
H430.9838−0.05170.85120.036*
C440.89578 (14)0.01675 (8)0.77911 (9)0.0230 (3)
H440.81780.00810.79860.028*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.01395 (9)0.01203 (9)0.01370 (9)0.00031 (6)0.00058 (6)0.00048 (6)
N10.0174 (5)0.0172 (5)0.0158 (5)0.0008 (4)0.0009 (4)−0.0002 (4)
N20.0189 (5)0.0131 (5)0.0187 (6)0.0015 (4)0.0020 (4)−0.0001 (4)
N30.0184 (5)0.0158 (5)0.0164 (5)−0.0007 (4)0.0005 (4)0.0001 (4)
N40.0172 (5)0.0167 (5)0.0185 (6)−0.0028 (4)0.0022 (4)0.0008 (4)
N50.0156 (5)0.0159 (5)0.0187 (6)0.0016 (4)−0.0004 (4)0.0014 (4)
N60.0146 (5)0.0142 (5)0.0157 (5)0.0006 (4)−0.0002 (4)0.0011 (4)
C10.0293 (8)0.0226 (7)0.0210 (7)0.0034 (6)0.0018 (6)−0.0043 (6)
C20.0451 (10)0.0344 (9)0.0177 (7)0.0057 (7)0.0008 (7)−0.0061 (6)
C30.0343 (9)0.0332 (8)0.0167 (7)0.0035 (7)−0.0012 (6)0.0030 (6)
C40.0197 (6)0.0201 (6)0.0173 (6)0.0004 (5)0.0007 (5)0.0032 (5)
C50.0194 (6)0.0171 (6)0.0210 (7)0.0013 (5)0.0016 (5)0.0056 (5)
C60.0248 (7)0.0143 (6)0.0235 (7)0.0035 (5)0.0030 (5)−0.0014 (5)
C70.0240 (7)0.0179 (6)0.0194 (7)0.0035 (5)0.0030 (5)−0.0030 (5)
C80.0240 (7)0.0205 (6)0.0208 (7)−0.0063 (5)−0.0013 (5)−0.0029 (5)
C90.0226 (7)0.0177 (6)0.0246 (7)−0.0060 (5)0.0018 (5)−0.0003 (5)
C100.0155 (6)0.0252 (7)0.0190 (6)−0.0004 (5)0.0019 (5)0.0005 (5)
C110.0157 (6)0.0218 (7)0.0203 (7)0.0034 (5)0.0004 (5)0.0005 (5)
C120.0221 (7)0.0244 (7)0.0255 (7)0.0083 (6)−0.0003 (6)−0.0013 (6)
C130.0296 (8)0.0172 (6)0.0305 (8)0.0071 (6)−0.0023 (6)−0.0013 (6)
C140.0225 (7)0.0161 (6)0.0240 (7)0.0016 (5)−0.0010 (5)0.0018 (5)
C150.0180 (6)0.0192 (6)0.0172 (6)−0.0014 (5)−0.0028 (5)0.0035 (5)
C160.0207 (7)0.0227 (7)0.0182 (7)−0.0035 (5)−0.0004 (5)0.0052 (5)
C170.0176 (6)0.0223 (7)0.0224 (7)−0.0029 (5)0.0008 (5)0.0024 (5)
C180.0162 (6)0.0243 (7)0.0208 (7)−0.0011 (5)−0.0044 (5)0.0022 (5)
C190.0180 (6)0.0188 (6)0.0160 (6)0.0002 (5)−0.0015 (5)0.0016 (5)
C200.0207 (7)0.0480 (10)0.0320 (9)−0.0113 (7)−0.0003 (6)0.0091 (8)
B10.0138 (6)0.0163 (6)0.0146 (7)0.0003 (5)0.0007 (5)−0.0004 (5)
C210.0142 (6)0.0181 (6)0.0182 (6)0.0031 (5)0.0009 (5)0.0025 (5)
C220.0208 (7)0.0314 (8)0.0199 (7)0.0002 (6)0.0025 (5)−0.0002 (6)
C230.0219 (7)0.0401 (9)0.0261 (8)0.0028 (6)0.0087 (6)0.0058 (7)
C240.0154 (7)0.0309 (8)0.0419 (10)0.0010 (6)0.0082 (6)0.0116 (7)
C250.0162 (6)0.0187 (6)0.0403 (9)0.0001 (5)0.0010 (6)0.0016 (6)
C260.0174 (6)0.0166 (6)0.0247 (7)0.0013 (5)0.0026 (5)0.0003 (5)
C270.0204 (6)0.0187 (6)0.0115 (6)0.0015 (5)−0.0006 (5)0.0001 (5)
C280.0236 (7)0.0205 (6)0.0179 (6)−0.0011 (5)0.0012 (5)−0.0003 (5)
C290.0352 (8)0.0212 (7)0.0204 (7)−0.0071 (6)0.0008 (6)−0.0006 (5)
C300.0485 (10)0.0171 (7)0.0174 (7)0.0023 (6)−0.0028 (6)−0.0008 (5)
C310.0353 (8)0.0242 (7)0.0168 (7)0.0110 (6)−0.0039 (6)−0.0033 (5)
C320.0236 (7)0.0226 (7)0.0160 (6)0.0040 (5)−0.0030 (5)−0.0027 (5)
C330.0126 (5)0.0170 (6)0.0150 (6)−0.0024 (4)0.0006 (4)−0.0005 (5)
C340.0211 (6)0.0210 (6)0.0171 (6)0.0035 (5)0.0000 (5)−0.0006 (5)
C350.0260 (7)0.0255 (7)0.0172 (7)0.0035 (6)−0.0024 (5)0.0022 (5)
C360.0231 (7)0.0236 (7)0.0146 (6)−0.0040 (5)0.0011 (5)−0.0013 (5)
C370.0220 (7)0.0169 (6)0.0184 (6)−0.0040 (5)0.0029 (5)−0.0028 (5)
C380.0182 (6)0.0152 (6)0.0166 (6)−0.0024 (5)0.0007 (5)0.0002 (5)
C390.0167 (6)0.0169 (6)0.0165 (6)0.0005 (5)−0.0009 (5)−0.0030 (5)
C400.0185 (6)0.0229 (6)0.0158 (6)0.0016 (5)0.0008 (5)−0.0042 (5)
C410.0171 (6)0.0262 (7)0.0260 (7)0.0042 (5)0.0002 (5)−0.0083 (6)
C420.0239 (7)0.0239 (7)0.0381 (9)0.0074 (6)−0.0083 (6)−0.0011 (6)
C430.0297 (8)0.0225 (7)0.0379 (9)0.0008 (6)−0.0063 (7)0.0104 (7)
C440.0201 (7)0.0202 (7)0.0284 (8)−0.0010 (5)−0.0027 (6)0.0045 (6)

Geometric parameters (Å, °)

Co1—N41.8952 (12)C19—H190.9500
Co1—N11.9043 (12)C20—H20A0.9800
Co1—N21.9156 (12)C20—H20B0.9800
Co1—N51.9320 (12)C20—H20C0.9800
Co1—N61.9581 (12)B1—C211.640 (2)
Co1—N32.0367 (12)B1—C391.644 (2)
N1—C11.3408 (18)B1—C331.649 (2)
N1—C41.3845 (18)B1—C271.653 (2)
N2—C51.2990 (19)C21—C261.401 (2)
N2—C61.4595 (18)C21—C221.408 (2)
N3—C71.4982 (18)C22—C231.391 (2)
N3—C81.5077 (18)C22—H220.9500
N3—H3N0.86 (2)C23—C241.389 (3)
N4—C101.3030 (18)C23—H230.9500
N4—C91.4537 (18)C24—C251.379 (2)
N5—C141.3460 (18)C24—H240.9500
N5—C111.3888 (18)C25—C261.398 (2)
N6—C191.3429 (17)C25—H250.9500
N6—C151.3488 (17)C26—H260.9500
C1—C21.400 (2)C27—C281.404 (2)
C1—H10.9500C27—C321.409 (2)
C2—C31.391 (2)C28—C291.397 (2)
C2—H20.9500C28—H280.9500
C3—C41.397 (2)C29—C301.390 (2)
C3—H30.9500C29—H290.9500
C4—C51.410 (2)C30—C311.384 (2)
C5—H50.9500C30—H300.9500
C6—C71.520 (2)C31—C321.399 (2)
C6—H6A0.9900C31—H310.9500
C6—H6B0.9900C32—H320.9500
C7—H7A0.9900C33—C341.4044 (19)
C7—H7B0.9900C33—C381.4055 (18)
C8—C91.528 (2)C34—C351.397 (2)
C8—H8A0.9900C34—H340.9500
C8—H8B0.9900C35—C361.388 (2)
C9—H9A0.9900C35—H350.9500
C9—H9B0.9900C36—C371.383 (2)
C10—C111.410 (2)C36—H360.9500
C10—H100.9500C37—C381.3948 (19)
C11—C121.399 (2)C37—H370.9500
C12—C131.392 (2)C38—H380.9500
C12—H120.9500C39—C441.403 (2)
C13—C141.403 (2)C39—C401.4079 (19)
C13—H130.9500C40—C411.392 (2)
C14—H140.9500C40—H400.9500
C15—C161.3768 (19)C41—C421.388 (2)
C15—H150.9500C41—H410.9500
C16—C171.390 (2)C42—C431.386 (2)
C16—H160.9500C42—H420.9500
C17—C181.388 (2)C43—C441.397 (2)
C17—C201.500 (2)C43—H430.9500
C18—C191.383 (2)C44—H440.9500
C18—H180.9500
N4—Co1—N192.00 (5)C17—C16—H16120.1
N4—Co1—N294.98 (5)C18—C17—C16117.14 (13)
N1—Co1—N282.11 (5)C18—C17—C20121.94 (14)
N4—Co1—N582.22 (5)C16—C17—C20120.92 (14)
N1—Co1—N588.67 (5)C19—C18—C17120.15 (13)
N2—Co1—N5170.28 (5)C19—C18—H18119.9
N4—Co1—N6170.80 (5)C17—C18—H18119.9
N1—Co1—N694.32 (5)N6—C19—C18122.55 (13)
N2—Co1—N692.51 (5)N6—C19—H19118.7
N5—Co1—N691.24 (5)C18—C19—H19118.7
N4—Co1—N382.26 (5)C17—C20—H20A109.5
N1—Co1—N3161.96 (5)C17—C20—H20B109.5
N2—Co1—N381.38 (5)H20A—C20—H20B109.5
N5—Co1—N3107.33 (5)C17—C20—H20C109.5
N6—Co1—N393.61 (5)H20A—C20—H20C109.5
C1—N1—C4107.35 (12)H20B—C20—H20C109.5
C1—N1—Co1139.14 (11)C21—B1—C39108.60 (11)
C4—N1—Co1113.49 (9)C21—B1—C33108.30 (11)
C5—N2—C6124.39 (12)C39—B1—C33109.21 (11)
C5—N2—Co1116.03 (10)C21—B1—C27110.93 (11)
C6—N2—Co1119.57 (9)C39—B1—C27112.38 (11)
C7—N3—C8112.61 (11)C33—B1—C27107.33 (11)
C7—N3—Co1106.46 (9)C26—C21—C22115.21 (13)
C8—N3—Co1109.79 (9)C26—C21—B1123.11 (12)
C7—N3—H3N105.5 (12)C22—C21—B1121.45 (13)
C8—N3—H3N105.4 (12)C23—C22—C21122.73 (15)
Co1—N3—H3N117.2 (13)C23—C22—H22118.6
C10—N4—C9121.58 (13)C21—C22—H22118.6
C10—N4—Co1115.59 (10)C24—C23—C22120.09 (15)
C9—N4—Co1114.36 (9)C24—C23—H23120.0
C14—N5—C11107.02 (12)C22—C23—H23120.0
C14—N5—Co1136.85 (10)C25—C24—C23119.04 (14)
C11—N5—Co1110.82 (9)C25—C24—H24120.5
C19—N6—C15117.30 (12)C23—C24—H24120.5
C19—N6—Co1123.13 (9)C24—C25—C26120.30 (15)
C15—N6—Co1119.57 (9)C24—C25—H25119.8
N1—C1—C2109.56 (14)C26—C25—H25119.8
N1—C1—H1125.2C25—C26—C21122.61 (14)
C2—C1—H1125.2C25—C26—H26118.7
C3—C2—C1107.70 (14)C21—C26—H26118.7
C3—C2—H2126.2C28—C27—C32114.92 (13)
C1—C2—H2126.2C28—C27—B1123.68 (12)
C2—C3—C4105.77 (14)C32—C27—B1120.97 (12)
C2—C3—H3127.1C29—C28—C27122.81 (14)
C4—C3—H3127.1C29—C28—H28118.6
N1—C4—C3109.61 (13)C27—C28—H28118.6
N1—C4—C5113.57 (13)C30—C29—C28120.31 (15)
C3—C4—C5136.77 (14)C30—C29—H29119.8
N2—C5—C4114.73 (13)C28—C29—H29119.8
N2—C5—H5122.6C31—C30—C29118.81 (14)
C4—C5—H5122.6C31—C30—H30120.6
N2—C6—C7105.73 (11)C29—C30—H30120.6
N2—C6—H6A110.6C30—C31—C32120.17 (15)
C7—C6—H6A110.6C30—C31—H31119.9
N2—C6—H6B110.6C32—C31—H31119.9
C7—C6—H6B110.6C31—C32—C27122.88 (15)
H6A—C6—H6B108.7C31—C32—H32118.6
N3—C7—C6109.11 (11)C27—C32—H32118.6
N3—C7—H7A109.9C34—C33—C38115.27 (12)
C6—C7—H7A109.9C34—C33—B1121.68 (12)
N3—C7—H7B109.9C38—C33—B1122.88 (12)
C6—C7—H7B109.9C35—C34—C33122.80 (13)
H7A—C7—H7B108.3C35—C34—H34118.6
N3—C8—C9109.74 (12)C33—C34—H34118.6
N3—C8—H8A109.7C36—C35—C34120.02 (14)
C9—C8—H8A109.7C36—C35—H35120.0
N3—C8—H8B109.7C34—C35—H35120.0
C9—C8—H8B109.7C37—C36—C35118.88 (13)
H8A—C8—H8B108.2C37—C36—H36120.6
N4—C9—C8103.34 (11)C35—C36—H36120.6
N4—C9—H9A111.1C36—C37—C38120.58 (13)
C8—C9—H9A111.1C36—C37—H37119.7
N4—C9—H9B111.1C38—C37—H37119.7
C8—C9—H9B111.1C37—C38—C33122.45 (13)
H9A—C9—H9B109.1C37—C38—H38118.8
N4—C10—C11114.98 (13)C33—C38—H38118.8
N4—C10—H10122.5C44—C39—C40115.12 (13)
C11—C10—H10122.5C44—C39—B1123.30 (12)
N5—C11—C12109.62 (13)C40—C39—B1121.57 (12)
N5—C11—C10112.69 (12)C41—C40—C39122.96 (14)
C12—C11—C10137.68 (14)C41—C40—H40118.5
C13—C12—C11106.03 (13)C39—C40—H40118.5
C13—C12—H12127.0C42—C41—C40120.02 (14)
C11—C12—H12127.0C42—C41—H41120.0
C12—C13—C14107.46 (13)C40—C41—H41120.0
C12—C13—H13126.3C43—C42—C41118.93 (14)
C14—C13—H13126.3C43—C42—H42120.5
N5—C14—C13109.86 (13)C41—C42—H42120.5
N5—C14—H14125.1C42—C43—C44120.34 (15)
C13—C14—H14125.1C42—C43—H43119.8
N6—C15—C16123.10 (13)C44—C43—H43119.8
N6—C15—H15118.4C43—C44—C39122.60 (14)
C16—C15—H15118.4C43—C44—H44118.7
C15—C16—C17119.72 (13)C39—C44—H44118.7
C15—C16—H16120.1
N4—Co1—N1—C1−85.68 (16)C14—N5—C11—C120.99 (17)
N2—Co1—N1—C1179.57 (17)Co1—N5—C11—C12159.84 (10)
N5—Co1—N1—C1−3.51 (16)C14—N5—C11—C10−179.68 (13)
N6—Co1—N1—C187.63 (16)Co1—N5—C11—C10−20.82 (15)
N3—Co1—N1—C1−156.52 (16)N4—C10—C11—N514.25 (19)
N4—Co1—N1—C492.32 (10)N4—C10—C11—C12−166.68 (17)
N2—Co1—N1—C4−2.43 (10)N5—C11—C12—C13−0.50 (17)
N5—Co1—N1—C4174.49 (10)C10—C11—C12—C13−179.59 (18)
N6—Co1—N1—C4−94.37 (10)C11—C12—C13—C14−0.16 (18)
N3—Co1—N1—C421.5 (2)C11—N5—C14—C13−1.09 (17)
N4—Co1—N2—C5−89.44 (11)Co1—N5—C14—C13−151.55 (12)
N1—Co1—N2—C51.90 (10)C12—C13—C14—N50.79 (18)
N6—Co1—N2—C595.92 (11)C19—N6—C15—C162.0 (2)
N3—Co1—N2—C5−170.81 (11)Co1—N6—C15—C16−177.98 (11)
N4—Co1—N2—C690.25 (11)N6—C15—C16—C17−0.8 (2)
N1—Co1—N2—C6−178.42 (11)C15—C16—C17—C18−1.2 (2)
N6—Co1—N2—C6−84.40 (11)C15—C16—C17—C20179.41 (15)
N3—Co1—N2—C68.88 (10)C16—C17—C18—C191.9 (2)
N4—Co1—N3—C7−125.83 (9)C20—C17—C18—C19−178.75 (15)
N1—Co1—N3—C7−53.5 (2)C15—N6—C19—C18−1.3 (2)
N2—Co1—N3—C7−29.56 (9)Co1—N6—C19—C18178.70 (11)
N5—Co1—N3—C7154.86 (9)C17—C18—C19—N6−0.7 (2)
N6—Co1—N3—C762.43 (9)C39—B1—C21—C26−97.53 (15)
N4—Co1—N3—C8−3.66 (9)C33—B1—C21—C2620.96 (17)
N1—Co1—N3—C868.66 (19)C27—B1—C21—C26138.50 (13)
N2—Co1—N3—C892.61 (10)C39—B1—C21—C2276.73 (16)
N5—Co1—N3—C8−82.97 (10)C33—B1—C21—C22−164.78 (13)
N6—Co1—N3—C8−175.40 (9)C27—B1—C21—C22−47.24 (17)
N1—Co1—N4—C1079.29 (11)C26—C21—C22—C231.0 (2)
N2—Co1—N4—C10161.54 (11)B1—C21—C22—C23−173.64 (14)
N5—Co1—N4—C10−9.10 (11)C21—C22—C23—C24−0.1 (2)
N3—Co1—N4—C10−117.88 (11)C22—C23—C24—C25−0.9 (2)
N1—Co1—N4—C9−132.03 (10)C23—C24—C25—C260.9 (2)
N2—Co1—N4—C9−49.77 (10)C24—C25—C26—C210.2 (2)
N5—Co1—N4—C9139.59 (10)C22—C21—C26—C25−1.1 (2)
N3—Co1—N4—C930.80 (10)B1—C21—C26—C25173.48 (13)
N4—Co1—N5—C14166.04 (16)C21—B1—C27—C28159.16 (13)
N1—Co1—N5—C1473.84 (15)C39—B1—C27—C2837.37 (18)
N6—Co1—N5—C14−20.45 (15)C33—B1—C27—C28−82.71 (15)
N3—Co1—N5—C14−114.62 (15)C21—B1—C27—C32−28.74 (17)
N4—Co1—N5—C1116.33 (10)C39—B1—C27—C32−150.53 (13)
N1—Co1—N5—C11−75.87 (10)C33—B1—C27—C3289.39 (14)
N6—Co1—N5—C11−170.16 (10)C32—C27—C28—C29−3.2 (2)
N3—Co1—N5—C1195.66 (10)B1—C27—C28—C29169.37 (13)
N1—Co1—N6—C1928.99 (11)C27—C28—C29—C300.9 (2)
N2—Co1—N6—C19−53.28 (11)C28—C29—C30—C311.7 (2)
N5—Co1—N6—C19117.75 (11)C29—C30—C31—C32−1.9 (2)
N3—Co1—N6—C19−134.79 (11)C30—C31—C32—C27−0.6 (2)
N1—Co1—N6—C15−151.02 (11)C28—C27—C32—C313.0 (2)
N2—Co1—N6—C15126.70 (11)B1—C27—C32—C31−169.73 (13)
N5—Co1—N6—C15−62.27 (11)C21—B1—C33—C3485.08 (15)
N3—Co1—N6—C1545.19 (11)C39—B1—C33—C34−156.82 (12)
C4—N1—C1—C20.81 (18)C27—B1—C33—C34−34.75 (16)
Co1—N1—C1—C2178.89 (13)C21—B1—C33—C38−90.05 (14)
N1—C1—C2—C3−0.6 (2)C39—B1—C33—C3828.05 (17)
C1—C2—C3—C40.1 (2)C27—B1—C33—C38150.13 (12)
C1—N1—C4—C3−0.77 (17)C38—C33—C34—C35−0.1 (2)
Co1—N1—C4—C3−179.40 (11)B1—C33—C34—C35−175.60 (13)
C1—N1—C4—C5−178.76 (13)C33—C34—C35—C360.1 (2)
Co1—N1—C4—C52.61 (15)C34—C35—C36—C37−0.3 (2)
C2—C3—C4—N10.43 (19)C35—C36—C37—C380.5 (2)
C2—C3—C4—C5177.73 (18)C36—C37—C38—C33−0.5 (2)
C6—N2—C5—C4179.39 (13)C34—C33—C38—C370.32 (19)
Co1—N2—C5—C4−0.94 (16)B1—C33—C38—C37175.74 (12)
N1—C4—C5—N2−1.10 (19)C21—B1—C39—C44−11.12 (18)
C3—C4—C5—N2−178.34 (17)C33—B1—C39—C44−129.03 (14)
C5—N2—C6—C7−166.34 (13)C27—B1—C39—C44111.99 (15)
Co1—N2—C6—C714.00 (15)C21—B1—C39—C40167.74 (12)
C8—N3—C7—C6−74.96 (14)C33—B1—C39—C4049.83 (16)
Co1—N3—C7—C645.40 (13)C27—B1—C39—C40−69.15 (16)
N2—C6—C7—N3−38.32 (15)C44—C39—C40—C41−1.5 (2)
C7—N3—C8—C996.87 (14)B1—C39—C40—C41179.59 (13)
Co1—N3—C8—C9−21.57 (14)C39—C40—C41—C421.3 (2)
C10—N4—C9—C897.92 (15)C40—C41—C42—C43−0.1 (2)
Co1—N4—C9—C8−48.69 (13)C41—C42—C43—C44−0.7 (3)
N3—C8—C9—N442.79 (15)C42—C43—C44—C390.5 (3)
C9—N4—C10—C11−146.56 (13)C40—C39—C44—C430.6 (2)
Co1—N4—C10—C11−0.32 (17)B1—C39—C44—C43179.51 (14)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2536).

References

  • Amirnasr, M., Schenk, K. J., Meghdadi, S. & Morshedi, M. (2006). Polyhedron, 25, 671–677.
  • Bruker (2003). SMART, SAINT, SADABS and XPREP Bruker AXS Inc., Madison, Wisconsin, USA.
  • Kwiatkowski, E., Kwiatkowski, M., Olechnowicz, A. & Bandoli, G. (1993). J. Crystallogr. Spectrosc. Res.23, 423–429.
  • Meghdadi, S., Daran, J.-C., Amirnasr, M. & Morshedi, M. (2007). Acta Cryst. E63, m982–m984.
  • Meghdadi, S., Schenk, K. J., Amirnasr, M. & Fadaee, F. (2008). Acta Cryst. E64, m479–m480. [PMC free article] [PubMed]
  • Miodragović, D. U., Bogdanović, G. A., Miodragović, Z. M., Radulović, M. D., Novaković, S. B., Kaluderović, G. N. & Kozlowski, H. (2006). J. Inorg. Biochem.100, 1568–1574. [PubMed]
  • Mishra, A., Kaushik, N. K., Verma, A. K. & Gupta, R. (2008). Eur. J. Med. Chem 43, 2189–2196. [PubMed]
  • Morshedi, M., Meghdadi, S. & Schenk, K. J. (2006). Acta Cryst. C62, m87–m89. [PubMed]
  • Nishinaga, A. & Tomita, H. (1980). J. Mol. Catal.7, 179–199.
  • Park, S., Mathur, V. K. & Planalp, R. P. (1998). Polyhedron, 17, 325–330.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Speiser, B. & Stahl, H. (1995). Angew. Chem. Int. Ed.34, 1086–1089.

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