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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1643–m1644.
Published online 2010 November 24. doi:  10.1107/S1600536810048191
PMCID: PMC3011730

Phenyl­hydrazinium (6-carb­oxy­pyridine-2-carboxyl­ato)(pyridine-2,6-dicarboxyl­ato)cobaltate(II)–pyridine-2,6-dicarb­oxy­lic acid–water (1/1/3)

Abstract

The asymmetric unit of the title compound, (C6H9N2)[Co(C7H3NO4)(C7H4NO4)]·C7H5NO4·3H2O, contains one (6-carb­oxy­pyridine-2-carboxyl­ato)(pyridine-2,6-dicarboxyl­ato)cobaltate(II) anion, one phenyl­hydrazinium cation, one pyridine-2,6-dicarb­oxy­lic acid mol­ecule and three uncoordin­ated water mol­ecules, part of which are disordered. The CoII ion is coordinated by a pyridine-2,6-dicarboxyl­ate ion and a 6-carb­oxy­pyridine-2-carboxyl­ate ligand almost perpendicular to each other [the angle between the least-squares planes is 87.38 (4)°] and is surrounded by two O atoms and two N atoms in the equatorial plane and two O atoms in axial positions, resulting in a distorted octa­hedral coordination geometry. There is an extensive three-dimensional network of O—H(...)O and N—H(...)O hydrogen bonds, which link the components.

Related literature

For related cobalt, copper and cadmium complexes containing 2,6-dicarboxyl­ato ligands, see: Aghabozorg et al. (2008 [triangle]); Aghabozorg et al. (2009 [triangle]); Moghimi et al. (2002 [triangle]). For an isotypic series of five related M(II) complexes, see: MacDonald et al. (2004 [triangle]). For the supra­molecular chemistry and crystal structures of five bis­(imidazolium 2,6-pyridine­dicarboxyl­ate)M(II) complexes, see: MacDonald et al. (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1643-scheme1.jpg

Experimental

Crystal data

  • (C6H9N2)[Co(C7H3NO4)(C7H4NO4)]·C7H5NO4·3H2O
  • M r = 720.47
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1643-efi1.jpg
  • a = 8.8019 (4) Å
  • b = 12.2378 (5) Å
  • c = 14.6559 (7) Å
  • α = 101.080 (2)°
  • β = 91.351 (3)°
  • γ = 98.749 (3)°
  • V = 1528.95 (12) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.64 mm−1
  • T = 293 K
  • 0.25 × 0.12 × 0.12 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000 [triangle]) T min = 0.825, T max = 0.999
  • 27004 measured reflections
  • 5526 independent reflections
  • 4198 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.167
  • S = 1.13
  • 5526 reflections
  • 462 parameters
  • 6 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.71 e Å−3
  • Δρmin = −0.78 e Å−3

Data collection: APEX2 (Bruker, 2003 [triangle]); cell refinement: SAINT (Bruker, 2003 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPII (Johnson, 1976 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048191/si2309sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048191/si2309Isup2.hkl

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

Acknowledgments

This work was supported by the Fundo Europeu de Desenvolvimento Regional-QREN-COMPETE through project PTDC/FIS/102284/2008-Fundação para a Ciência e a Tecnologia (FCT).

supplementary crystallographic information

Comment

Many complexes containing pyridine-2,6-dicarboxylate, CoII ions and various bases have been reported (Aghabozorg et al. 2008, 2009; Moghimi et al., 2002; MacDonald et al., 2004, 2000).

In the title compound (I), Fig. 1, the metal ion CoII is six-coordinated by two pyridine-2,6-dicarboxylate ligands, with -2 and -1 negative charges (Table 1). Both ligands are tridentate and the coordination sphere around the cobalt is a distorted octahedral with the N—Co—N angle equal to 177.68 (9)°. The angle between the least-squares plane of the non-H atoms of the two ligands is 87.38 (4)°. Each complex of total charge -1 is accompanied in the asymmetric unit cell by one phenylhydrazinium ion as a counter ion, a neutral pyridine-2,6-dicarboxylic acid molecule and three water molecules. In the cation the terminal N4 is deviated by 1.188 (3)Å from the C22—C27 plane. The bond angle sum around N5 is 327°, indicative of a sp3 hybridization for this atom. There is an extensive three-dimensional network of H-bonds linking the molecules and ions together. Water O13 links the cobalt complexes along the b axis and water O14 links the cobalt complexes along the a axis. The neutral acidic molecule is H-bonded to the complex and the cation shares the NH and NH3 hydrogen atoms with two symmetry related complexes and the neutral acid molecule (Table 2 and Fig. 2).

Experimental

From a solution of phenylhydrazine (0.4 mmol) and of pyridine-2,6-dicarboxylic acid (0.4 mmol) in THF (30 ml), a white precipitate was obtained. By mixing the precipitate with cobalt (II) nitrate (0.2 mmol) in water (25 ml), brown crystals of the title compound were obtained after allowing the mixture to stand for 2 weeks at room temperature.

Refinement

The occupancy of water O atoms, O15 and O16, refined to near 50%, so that at the final stages of refinement the sum of their occupancies was set to one. H atoms bound to C atoms were placed at calculated positions and were treated as riding on the parent atoms with C—H = 0.93 Å (aromatic) and 0.98 Å (CH) and with Uiso(H) = 1.2 Ueq(C). H atoms of water molecules O13 an O14 were located in a difference Fourier map and refined as riding with O—H = 0.85 (1) Å, H—H = 1.34 (1) Å and Uiso(H) = 1.5Ueq(O). The H atoms of the remaining water molecule disordered over two sites could not be located. H atoms of hydroxyl and hydrazinium groups were located in a difference electron density map but O–H were refined using AFIX 147 and NH3 H atoms using AFIX 137 in SHELXL97. The coordinates of H atom attached to N5 were freely refined, Uiso(H5) = 1.2 Ueq(N5).

Figures

Fig. 1.
ORTEPII (Johnson, 1976) plot of the title compound. Displacement ellipsoids are drawn at the 50% level.
Fig. 2.
Packing of the molecules in the unit cell showing the H-bonds as dashed lines. H atoms not involved in H-bonding were omitted for clarity. Also omitted were the disordered water O atoms.

Crystal data

(C6H9N2)[Co(C7H3NO4)(C7H4NO4)]·C7H5NO4·3H2OZ = 2
Mr = 720.47F(000) = 742
Triclinic, P1Dx = 1.565 Mg m3
a = 8.8019 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.2378 (5) ÅCell parameters from 8005 reflections
c = 14.6559 (7) Åθ = 2.8–25.2°
α = 101.080 (2)°µ = 0.64 mm1
β = 91.351 (3)°T = 293 K
γ = 98.749 (3)°Block, brown
V = 1528.95 (12) Å30.25 × 0.12 × 0.12 mm

Data collection

Bruker APEX CCD area-detector diffractometer5526 independent reflections
Radiation source: fine-focus sealed tube4198 reflections with I > 2σ(I)
graphiteRint = 0.038
[var phi] and ω scansθmax = 25.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)h = −10→10
Tmin = 0.825, Tmax = 0.999k = −14→14
27004 measured reflectionsl = −17→17

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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H atoms treated by a mixture of independent and constrained refinement
S = 1.13w = 1/[σ2(Fo2) + (0.1037P)2] where P = (Fo2 + 2Fc2)/3
5526 reflections(Δ/σ)max = 0.002
462 parametersΔρmax = 0.71 e Å3
6 restraintsΔρmin = −0.78 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
Co10.08241 (5)0.11526 (3)0.27416 (3)0.03986 (15)
N10.0353 (3)0.20143 (19)0.17546 (17)0.0321 (5)
N20.1315 (3)0.0232 (2)0.36950 (16)0.0333 (6)
O10.1988 (3)0.04183 (18)0.15618 (15)0.0439 (5)
O20.2202 (3)0.03896 (18)0.00472 (16)0.0467 (6)
O3−0.0290 (3)0.2509 (2)0.34757 (17)0.0604 (7)
O4−0.1504 (3)0.3913 (2)0.32449 (19)0.0718 (8)
O5−0.1078 (3)−0.0133 (2)0.25722 (17)0.0549 (6)
O6−0.2095 (3)−0.1669 (2)0.30695 (18)0.0554 (6)
O70.3082 (3)0.2062 (2)0.35125 (17)0.0533 (6)
O80.4774 (3)0.1909 (2)0.46295 (19)0.0645 (7)
H80.51930.25220.45380.097*
O130.7224 (4)0.5896 (2)0.2939 (2)0.0735 (8)
H13A0.767 (4)0.6505 (12)0.328 (2)0.110*
H13B0.765 (3)0.5383 (15)0.310 (3)0.110*
O140.6225 (4)0.3733 (3)0.4384 (2)0.0911 (10)
H14A0.696 (2)0.384 (3)0.4033 (16)0.137*
H14B0.606 (4)0.4388 (13)0.464 (3)0.137*
O150.7032 (9)0.5579 (4)0.5692 (4)0.111 (3)0.600 (6)
O160.0711 (12)0.3917 (6)0.5180 (5)0.100 (4)0.400 (6)
C10.1723 (3)0.0746 (2)0.0823 (2)0.0344 (7)
C20.0767 (3)0.1683 (2)0.0894 (2)0.0315 (6)
C30.0373 (4)0.2194 (3)0.0181 (2)0.0388 (7)
H30.06510.1947−0.04240.047*
C4−0.0448 (4)0.3087 (3)0.0388 (2)0.0430 (8)
H4−0.07250.3448−0.00790.052*
C5−0.0851 (4)0.3435 (3)0.1288 (2)0.0437 (8)
H5−0.13930.40350.14370.052*
C6−0.0434 (3)0.2873 (2)0.1966 (2)0.0355 (7)
C7−0.0777 (4)0.3123 (3)0.2975 (2)0.0472 (8)
C8−0.1070 (4)−0.0855 (3)0.3071 (2)0.0413 (8)
C90.0315 (3)−0.0679 (2)0.3749 (2)0.0357 (7)
C100.0559 (4)−0.1344 (3)0.4379 (2)0.0417 (8)
H10−0.0138−0.19880.44040.050*
C110.1854 (4)−0.1037 (3)0.4969 (2)0.0465 (8)
H110.2037−0.14740.54010.056*
C120.2878 (4)−0.0085 (3)0.4920 (2)0.0438 (8)
H120.37550.01370.53180.053*
C130.2571 (3)0.0526 (3)0.4267 (2)0.0388 (7)
C140.3519 (4)0.1574 (3)0.4096 (2)0.0441 (8)
N30.5452 (3)0.71742 (19)0.98841 (17)0.0336 (6)
O90.3803 (3)0.88505 (18)1.00552 (14)0.0423 (5)
H90.33520.93911.00610.063*
O100.3851 (3)0.88449 (19)0.85355 (16)0.0494 (6)
O110.6360 (3)0.6510 (2)1.14056 (17)0.0620 (7)
H11A0.68070.63531.18490.093*
O120.7558 (3)0.5215 (2)1.0602 (2)0.0749 (8)
C160.4987 (3)0.7465 (2)0.9112 (2)0.0354 (7)
C170.5231 (4)0.6919 (3)0.8224 (2)0.0458 (8)
H170.48900.71640.77040.055*
C180.5987 (4)0.6008 (3)0.8129 (3)0.0550 (9)
H180.61610.56170.75410.066*
C190.6486 (4)0.5682 (3)0.8917 (3)0.0475 (8)
H190.70060.50680.88720.057*
C200.6203 (3)0.6280 (2)0.9773 (2)0.0378 (7)
C150.4154 (3)0.8466 (2)0.9206 (2)0.0353 (7)
C210.6782 (4)0.5948 (3)1.0634 (3)0.0456 (8)
N40.5745 (3)0.8905 (2)0.17482 (17)0.0379 (6)
H4A0.63510.86160.21010.057*
H4B0.62560.95370.16190.057*
H4C0.54590.84100.12210.057*
N50.4388 (3)0.9152 (2)0.22451 (19)0.0416 (6)
H5A0.373 (4)0.950 (3)0.186 (2)0.050*
C220.3461 (4)0.8152 (2)0.2400 (2)0.0367 (7)
C230.1992 (4)0.7818 (3)0.1991 (2)0.0488 (9)
H230.16240.82240.15820.059*
C240.1081 (4)0.6894 (3)0.2185 (3)0.0580 (10)
H240.00910.66770.19100.070*
C250.1611 (5)0.6277 (3)0.2787 (3)0.0599 (11)
H250.09900.56440.29130.072*
C260.3070 (5)0.6615 (3)0.3196 (3)0.0566 (10)
H260.34320.62080.36060.068*
C270.4004 (4)0.7545 (3)0.3010 (2)0.0483 (8)
H270.49910.77650.32900.058*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.0464 (3)0.0381 (2)0.0397 (3)0.0132 (2)0.0000 (2)0.01435 (19)
N10.0308 (12)0.0296 (12)0.0389 (14)0.0099 (10)0.0025 (11)0.0103 (10)
N20.0325 (13)0.0362 (13)0.0320 (13)0.0088 (11)0.0009 (11)0.0062 (10)
O10.0504 (13)0.0434 (12)0.0459 (13)0.0248 (10)0.0005 (10)0.0152 (10)
O20.0571 (14)0.0433 (12)0.0446 (13)0.0251 (11)0.0051 (11)0.0068 (10)
O30.0909 (19)0.0574 (15)0.0440 (14)0.0353 (14)0.0181 (13)0.0174 (12)
O40.104 (2)0.0577 (15)0.0709 (18)0.0476 (15)0.0441 (16)0.0228 (13)
O50.0472 (14)0.0600 (15)0.0607 (15)0.0037 (12)−0.0168 (12)0.0258 (13)
O60.0474 (14)0.0505 (14)0.0652 (16)−0.0032 (12)−0.0096 (12)0.0138 (12)
O70.0584 (15)0.0524 (14)0.0492 (14)−0.0025 (12)−0.0069 (12)0.0202 (12)
O80.0483 (15)0.0739 (19)0.0680 (17)−0.0122 (13)−0.0157 (13)0.0254 (15)
O130.090 (2)0.0642 (17)0.0686 (19)0.0135 (16)−0.0180 (16)0.0220 (15)
O140.097 (2)0.076 (2)0.088 (2)−0.0165 (18)0.0360 (19)0.0076 (18)
O150.196 (7)0.056 (3)0.082 (4)0.050 (4)−0.017 (4)−0.006 (3)
O160.175 (9)0.061 (5)0.050 (5)−0.001 (5)−0.032 (5)−0.002 (4)
C10.0299 (15)0.0291 (15)0.0440 (18)0.0072 (12)−0.0010 (13)0.0050 (13)
C20.0296 (14)0.0272 (14)0.0377 (17)0.0064 (12)−0.0018 (12)0.0055 (12)
C30.0424 (17)0.0395 (17)0.0370 (17)0.0112 (14)0.0000 (14)0.0102 (14)
C40.0484 (19)0.0414 (17)0.0454 (19)0.0167 (15)−0.0020 (15)0.0170 (15)
C50.0425 (18)0.0367 (16)0.058 (2)0.0165 (14)0.0052 (16)0.0165 (15)
C60.0357 (16)0.0267 (14)0.0470 (18)0.0088 (12)0.0075 (14)0.0111 (13)
C70.057 (2)0.0402 (18)0.050 (2)0.0163 (16)0.0156 (17)0.0155 (15)
C80.0385 (17)0.0402 (18)0.0445 (19)0.0089 (15)−0.0032 (14)0.0055 (15)
C90.0366 (16)0.0356 (16)0.0352 (16)0.0121 (13)0.0035 (13)0.0028 (13)
C100.0446 (18)0.0393 (17)0.0446 (19)0.0113 (14)0.0047 (15)0.0126 (14)
C110.0488 (19)0.053 (2)0.0465 (19)0.0175 (16)0.0058 (16)0.0241 (16)
C120.0386 (17)0.062 (2)0.0354 (17)0.0181 (16)−0.0019 (14)0.0139 (15)
C130.0322 (16)0.0497 (18)0.0360 (17)0.0120 (14)0.0028 (13)0.0081 (14)
C140.0376 (18)0.052 (2)0.0418 (19)0.0032 (15)0.0008 (15)0.0095 (16)
N30.0318 (13)0.0267 (12)0.0436 (15)0.0073 (10)0.0022 (11)0.0081 (10)
O90.0508 (13)0.0435 (12)0.0390 (12)0.0241 (10)0.0050 (10)0.0109 (10)
O100.0688 (16)0.0441 (13)0.0418 (13)0.0214 (12)0.0017 (11)0.0150 (10)
O110.0911 (19)0.0541 (14)0.0491 (15)0.0348 (14)−0.0068 (14)0.0137 (12)
O120.090 (2)0.0721 (17)0.083 (2)0.0550 (16)0.0105 (16)0.0316 (15)
C160.0360 (16)0.0297 (15)0.0401 (17)0.0055 (13)0.0023 (13)0.0058 (13)
C170.053 (2)0.0431 (18)0.0412 (19)0.0128 (16)0.0045 (16)0.0041 (15)
C180.065 (2)0.049 (2)0.049 (2)0.0212 (18)0.0111 (18)−0.0050 (17)
C190.0490 (19)0.0331 (16)0.060 (2)0.0140 (15)0.0082 (17)0.0027 (15)
C200.0343 (16)0.0282 (15)0.0509 (19)0.0073 (13)0.0026 (14)0.0063 (13)
C150.0331 (16)0.0316 (15)0.0415 (18)0.0046 (13)0.0010 (13)0.0085 (13)
C210.0457 (19)0.0328 (16)0.062 (2)0.0110 (15)0.0006 (16)0.0145 (15)
N40.0375 (14)0.0356 (13)0.0411 (15)0.0069 (11)−0.0027 (11)0.0089 (11)
N50.0447 (15)0.0362 (14)0.0466 (16)0.0124 (12)0.0043 (13)0.0095 (12)
C220.0430 (17)0.0337 (16)0.0337 (16)0.0103 (14)0.0060 (14)0.0032 (13)
C230.048 (2)0.049 (2)0.048 (2)0.0101 (17)−0.0021 (16)0.0062 (16)
C240.048 (2)0.056 (2)0.065 (3)0.0004 (18)0.0050 (18)0.0026 (19)
C250.072 (3)0.041 (2)0.061 (2)−0.0036 (19)0.025 (2)0.0023 (18)
C260.081 (3)0.046 (2)0.046 (2)0.014 (2)0.0116 (19)0.0153 (16)
C270.055 (2)0.049 (2)0.0430 (19)0.0095 (17)−0.0043 (16)0.0129 (16)

Geometric parameters (Å, °)

Co1—N12.017 (2)C12—C131.368 (4)
Co1—N22.033 (2)C12—H120.9300
Co1—O52.090 (2)C13—C141.487 (5)
Co1—O12.148 (2)N3—C161.323 (4)
Co1—O32.175 (2)N3—C201.348 (3)
Co1—O72.281 (2)O9—C151.304 (4)
N1—C21.325 (4)O9—H90.8200
N1—C61.337 (3)O10—C151.206 (4)
N2—C91.327 (4)O11—C211.300 (4)
N2—C131.332 (4)O11—H11A0.8200
O1—C11.254 (4)O12—C211.202 (4)
O2—C11.244 (4)C16—C171.382 (4)
O3—C71.257 (4)C16—C151.507 (4)
O4—C71.247 (4)C17—C181.369 (4)
O5—C81.251 (4)C17—H170.9300
O6—C81.238 (4)C18—C191.376 (5)
O7—C141.219 (4)C18—H180.9300
O8—C141.303 (4)C19—C201.375 (4)
O8—H80.8200C19—H190.9300
O13—H13A0.85 (2)C20—C211.498 (4)
O13—H13B0.85 (3)N4—N51.454 (3)
O14—H14A0.85 (2)N4—H4A0.8900
O14—H14B0.85 (3)N4—H4B0.8900
C1—C21.512 (4)N4—H4C0.8900
C2—C31.380 (4)N5—C221.424 (4)
C3—C41.390 (4)N5—H5A0.99 (3)
C3—H30.9300C22—C231.380 (5)
C4—C51.377 (5)C22—C271.386 (4)
C4—H40.9300C23—C241.365 (5)
C5—C61.385 (4)C23—H230.9300
C5—H50.9300C24—C251.382 (5)
C6—C71.500 (4)C24—H240.9300
C8—C91.517 (4)C25—C261.373 (6)
C9—C101.375 (4)C25—H250.9300
C10—C111.373 (5)C26—C271.376 (5)
C10—H100.9300C26—H260.9300
C11—C121.376 (5)C27—H270.9300
C11—H110.9300
N1—Co1—N2177.68 (9)C13—C12—C11118.1 (3)
N1—Co1—O5102.10 (9)C13—C12—H12121.0
N2—Co1—O577.14 (9)C11—C12—H12121.0
N1—Co1—O176.28 (8)N2—C13—C12122.1 (3)
N2—Co1—O1101.57 (8)N2—C13—C14111.1 (3)
O5—Co1—O196.18 (10)C12—C13—C14126.8 (3)
N1—Co1—O375.72 (9)O7—C14—O8125.3 (3)
N2—Co1—O3106.53 (9)O7—C14—C13120.2 (3)
O5—Co1—O397.68 (10)O8—C14—C13114.5 (3)
O1—Co1—O3150.78 (9)C16—N3—C20116.3 (3)
N1—Co1—O7107.38 (9)C15—O9—H9109.5
N2—Co1—O773.46 (9)C21—O11—H11A109.5
O5—Co1—O7150.47 (9)N3—C16—C17124.3 (3)
O1—Co1—O792.35 (9)N3—C16—C15118.0 (3)
O3—Co1—O788.12 (10)C17—C16—C15117.7 (3)
C2—N1—C6121.0 (2)C18—C17—C16118.3 (3)
C2—N1—Co1119.22 (18)C18—C17—H17120.8
C6—N1—Co1119.7 (2)C16—C17—H17120.8
C9—N2—C13119.9 (3)C17—C18—C19118.9 (3)
C9—N2—Co1117.7 (2)C17—C18—H18120.5
C13—N2—Co1122.4 (2)C19—C18—H18120.5
C1—O1—Co1115.10 (17)C20—C19—C18118.8 (3)
C7—O3—Co1115.3 (2)C20—C19—H19120.6
C8—O5—Co1116.8 (2)C18—C19—H19120.6
C14—O7—Co1112.8 (2)N3—C20—C19123.3 (3)
C14—O8—H8109.5N3—C20—C21117.7 (3)
H13A—O13—H13B105 (3)C19—C20—C21119.0 (3)
H14A—O14—H14B105 (3)O10—C15—O9125.0 (3)
O2—C1—O1126.1 (3)O10—C15—C16120.9 (3)
O2—C1—C2117.5 (3)O9—C15—C16114.1 (3)
O1—C1—C2116.4 (3)O12—C21—O11123.5 (3)
N1—C2—C3121.4 (3)O12—C21—C20122.3 (3)
N1—C2—C1112.3 (2)O11—C21—C20114.2 (3)
C3—C2—C1126.4 (3)N5—N4—H4A109.5
C2—C3—C4118.3 (3)N5—N4—H4B109.5
C2—C3—H3120.9H4A—N4—H4B109.5
C4—C3—H3120.9N5—N4—H4C109.5
C5—C4—C3119.8 (3)H4A—N4—H4C109.5
C5—C4—H4120.1H4B—N4—H4C109.5
C3—C4—H4120.1C22—N5—N4111.7 (2)
C4—C5—C6118.7 (3)C22—N5—H5A106 (2)
C4—C5—H5120.7N4—N5—H5A109.6 (19)
C6—C5—H5120.7C23—C22—C27119.7 (3)
N1—C6—C5120.8 (3)C23—C22—N5120.5 (3)
N1—C6—C7112.8 (2)C27—C22—N5119.6 (3)
C5—C6—C7126.4 (3)C24—C23—C22120.1 (3)
O4—C7—O3125.9 (3)C24—C23—H23120.0
O4—C7—C6117.9 (3)C22—C23—H23120.0
O3—C7—C6116.2 (3)C23—C24—C25120.8 (4)
O6—C8—O5125.9 (3)C23—C24—H24119.6
O6—C8—C9118.3 (3)C25—C24—H24119.6
O5—C8—C9115.8 (3)C26—C25—C24118.9 (4)
N2—C9—C10121.3 (3)C26—C25—H25120.5
N2—C9—C8112.5 (3)C24—C25—H25120.5
C10—C9—C8126.2 (3)C25—C26—C27121.1 (4)
C11—C10—C9118.7 (3)C25—C26—H26119.4
C11—C10—H10120.7C27—C26—H26119.4
C9—C10—H10120.7C26—C27—C22119.3 (3)
C10—C11—C12120.0 (3)C26—C27—H27120.3
C10—C11—H11120.0C22—C27—H27120.3
C12—C11—H11120.0
N2—Co1—N1—C2−15 (2)Co1—O3—C7—O4176.8 (3)
O5—Co1—N1—C2−86.1 (2)Co1—O3—C7—C6−3.6 (4)
O1—Co1—N1—C27.4 (2)N1—C6—C7—O4179.8 (3)
O3—Co1—N1—C2178.9 (2)C5—C6—C7—O4−0.3 (5)
O7—Co1—N1—C295.6 (2)N1—C6—C7—O30.1 (4)
N2—Co1—N1—C6161 (2)C5—C6—C7—O3−180.0 (3)
O5—Co1—N1—C690.7 (2)Co1—O5—C8—O6179.7 (3)
O1—Co1—N1—C6−175.8 (2)Co1—O5—C8—C91.3 (4)
O3—Co1—N1—C6−4.3 (2)C13—N2—C9—C10−1.0 (4)
O7—Co1—N1—C6−87.7 (2)Co1—N2—C9—C10−179.7 (2)
N1—Co1—N2—C9−70 (2)C13—N2—C9—C8177.8 (2)
O5—Co1—N2—C91.2 (2)Co1—N2—C9—C8−0.9 (3)
O1—Co1—N2—C9−92.6 (2)O6—C8—C9—N2−178.8 (3)
O3—Co1—N2—C995.5 (2)O5—C8—C9—N2−0.3 (4)
O7—Co1—N2—C9178.4 (2)O6—C8—C9—C10−0.1 (5)
N1—Co1—N2—C13111 (2)O5—C8—C9—C10178.4 (3)
O5—Co1—N2—C13−177.5 (2)N2—C9—C10—C111.1 (5)
O1—Co1—N2—C1388.8 (2)C8—C9—C10—C11−177.5 (3)
O3—Co1—N2—C13−83.1 (2)C9—C10—C11—C12−0.3 (5)
O7—Co1—N2—C13−0.3 (2)C10—C11—C12—C13−0.6 (5)
N1—Co1—O1—C1−7.2 (2)C9—N2—C13—C120.0 (4)
N2—Co1—O1—C1171.9 (2)Co1—N2—C13—C12178.7 (2)
O5—Co1—O1—C193.8 (2)C9—N2—C13—C14−179.4 (2)
O3—Co1—O1—C1−24.1 (3)Co1—N2—C13—C14−0.7 (3)
O7—Co1—O1—C1−114.5 (2)C11—C12—C13—N20.8 (5)
N1—Co1—O3—C74.2 (3)C11—C12—C13—C14−179.9 (3)
N2—Co1—O3—C7−175.2 (3)Co1—O7—C14—O8179.7 (3)
O5—Co1—O3—C7−96.4 (3)Co1—O7—C14—C13−2.4 (4)
O1—Co1—O3—C721.3 (4)N2—C13—C14—O72.2 (4)
O7—Co1—O3—C7112.7 (3)C12—C13—C14—O7−177.2 (3)
N1—Co1—O5—C8176.4 (2)N2—C13—C14—O8−179.7 (3)
N2—Co1—O5—C8−1.4 (2)C12—C13—C14—O80.9 (5)
O1—Co1—O5—C899.1 (2)C20—N3—C16—C17−0.4 (4)
O3—Co1—O5—C8−106.7 (2)C20—N3—C16—C15−179.5 (3)
O7—Co1—O5—C8−6.8 (4)N3—C16—C17—C180.8 (5)
N1—Co1—O7—C14−176.3 (2)C15—C16—C17—C18179.9 (3)
N2—Co1—O7—C141.4 (2)C16—C17—C18—C19−0.7 (5)
O5—Co1—O7—C147.0 (4)C17—C18—C19—C200.2 (5)
O1—Co1—O7—C14−99.9 (2)C16—N3—C20—C19−0.1 (5)
O3—Co1—O7—C14109.3 (2)C16—N3—C20—C21178.4 (3)
Co1—O1—C1—O2−175.8 (2)C18—C19—C20—N30.2 (5)
Co1—O1—C1—C26.0 (3)C18—C19—C20—C21−178.3 (3)
C6—N1—C2—C3−1.4 (4)N3—C16—C15—O10171.8 (3)
Co1—N1—C2—C3175.3 (2)C17—C16—C15—O10−7.3 (5)
C6—N1—C2—C1176.7 (3)N3—C16—C15—O9−8.7 (4)
Co1—N1—C2—C1−6.6 (3)C17—C16—C15—O9172.1 (3)
O2—C1—C2—N1−178.4 (3)N3—C20—C21—O12−174.5 (3)
O1—C1—C2—N10.0 (4)C19—C20—C21—O124.1 (5)
O2—C1—C2—C3−0.4 (5)N3—C20—C21—O116.2 (4)
O1—C1—C2—C3178.0 (3)C19—C20—C21—O11−175.2 (3)
N1—C2—C3—C41.2 (5)N4—N5—C22—C23−115.4 (3)
C1—C2—C3—C4−176.6 (3)N4—N5—C22—C2768.4 (4)
C2—C3—C4—C5−0.2 (5)C27—C22—C23—C24−0.1 (5)
C3—C4—C5—C6−0.6 (5)N5—C22—C23—C24−176.3 (3)
C2—N1—C6—C50.6 (4)C22—C23—C24—C25−0.3 (5)
Co1—N1—C6—C5−176.1 (2)C23—C24—C25—C260.7 (6)
C2—N1—C6—C7−179.5 (3)C24—C25—C26—C27−0.5 (5)
Co1—N1—C6—C73.8 (3)C25—C26—C27—C220.1 (5)
C4—C5—C6—N10.4 (5)C23—C22—C27—C260.2 (5)
C4—C5—C6—C7−179.5 (3)N5—C22—C27—C26176.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O8—H8···O140.821.672.491 (4)174
O13—H13A···O6i0.85 (2)2.29 (2)2.917 (4)131 (3)
O13—H13B···O4ii0.85 (3)2.09 (2)2.926 (4)168 (3)
O14—H14A···O4ii0.85 (2)1.80 (2)2.645 (4)174 (3)
O14—H14B···O150.85 (3)1.98 (4)2.658 (6)136 (4)
O9—H9···O2iii0.821.702.520 (3)173
O11—H11A···O13iv0.821.842.634 (4)163
N4—H4A···O6i0.892.062.935 (3)167
N4—H4A···O5i0.892.532.993 (3)113
N4—H4A···O11v0.892.583.011 (3)110
N4—H4B···O10vi0.892.052.834 (3)146
N4—H4C···O9v0.892.412.964 (3)121
N5—H5A···O1vii0.99 (3)2.12 (3)3.060 (3)158 (3)

Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z; (iii) x, y+1, z+1; (iv) x, y, z+1; (v) x, y, z−1; (vi) −x+1, −y+2, −z+1; (vii) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2309).

References

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