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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m100.
Published online 2007 December 6. doi:  10.1107/S1600536807064495
PMCID: PMC2915054

[2,6-Dioxo-1,2,3,6-tetra­hydro­pyrim­idine-4-carboxyl­ato(2−)]bis(pyrazino[2,3-f][1,10]phenanthroline)cobalt(II) dihydrate

Abstract

The title complex, [Co(C5H2N2O4)(C14H8N4)2]·2H2O, features a slightly distorted octa­hedral geometry for Co due to the sterical requirements of the orotic acid and pyrazino[2,3-f][1,10]phenanthroline ligands. Inter­molecular hydrogen bonding between the uncoordinated water mol­ecules and the ligand stablizes the structure of the complex.

Related literature

For related literature, see: Darensbourg et al. (1998 [triangle]); Lieberman et al. (1955 [triangle]); Lalioti et al. (1998 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m100-scheme1.jpg

Experimental

Crystal data

  • [Co(C5H2N2O4)(C14H8N4)2]·2H2O
  • M r = 713.54
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m100-efi1.jpg
  • a = 15.9468 (7) Å
  • b = 13.3765 (6) Å
  • c = 15.5661 (7) Å
  • β = 117.5610 (10)°
  • V = 2943.6 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.65 mm−1
  • T = 293 (2) K
  • 0.16 × 0.12 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.903, T max = 0.938
  • 32977 measured reflections
  • 5185 independent reflections
  • 4601 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.105
  • S = 1.00
  • 5185 reflections
  • 451 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a [triangle]); molecular graphics: SHELXTL (Sheldrick, 1997b [triangle]); software used to prepare material for publication: SHELXTL.

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064495/fi2050sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064495/fi2050Isup2.hkl

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

Acknowledgments

The authors thank the Postgraduate Foundation of Taishan University (No. Y06–2–12) for financial support.

supplementary crystallographic information

Comment

Orotic acid is an important pyrimidine derivative as the effective precursor in the biosythesis of the pyrimidine base of nucleic acids in living organisms and plays a unique role in bioinorganic and pharmaceutical chemistry (Lieberman et al., 1955). Aside from the biological interest, orotic acid is also interesting in coordination chemistry (Lalioti et al., 1998). In this contribution, the title compound (I) was synthesized and its crystal structure determined (Fig. 1 and Table 1). The central Co is coordinated by five nitrogen atoms (four from pyrazino[2,3-f][1,10]phenanthroline ligand and one from orotic acid ligand) and one carboxylate oxygen from the orotic acid ligand,yielding a slightly distorted octahedral coordination geometry. The geometric parameters are in good agreement with those found in literature (Darensbourg et al., 1998). The intermolecular hydrogen bonding between the uncoordinated water molecules and the ligand stablizes the structure of the complex (Fig. 2).

Experimental

The orotic acid (Lancaster, 98%) and solvents were commercially available, and they were used without further purification. The orotic acid (0.035 g, 0.2 mmol) CoCl2 6H2O (0.047 g, 0.2 mmol) and pyrazino[2,3-f][1,10]phenanthroline were added to 40 ml EtOH-water(1:2 V:V) and heated to 353 K and stirred for 20 min.A few drops of ammonia were added to adjust the pH value to about 6 and then the resulting mixture was filtered. Orange single crystals were obtained after a few days. Yield, 0.096 g, 75%. m.p. 450–452 K.

Analysis found: C 55.50, H 3.14, N 19.58, O 13.42%; C33H22N10O6Co requires: C 55.55, H 3.11, N 19.63, O 13.45%.

Refinement

All H atoms were initially located in diffrence Fourier map. The C, O and N bound H atoms were then constrained to an ideal geometry, with C—H = 0.93 Å and refined as riding with Uiso(H) = 1.2Ueq(C-aromatic) and with the O—H = 0.8494 - 0.8512 Å, N—H = 0.8321 Å and refined as riding with Uiso(H) = 1.2Ueq(O, N).

Figures

Fig. 1.
The structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme. The H atoms are omitted for clarity.
Fig. 2.
The intermolecular hydrogen bonding in the complex.

Crystal data

[Co(C5H2N2O4)(C14H8N4)2]·2H2OF000 = 1460
Mr = 713.54Dx = 1.610 Mg m3
Monoclinic, P2(1)/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 14858 reflections
a = 15.9468 (7) Åθ = 2.6–28.1º
b = 13.3765 (6) ŵ = 0.65 mm1
c = 15.5661 (7) ÅT = 293 (2) K
β = 117.5610 (10)ºBlock, orange
V = 2943.6 (2) Å30.16 × 0.12 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer5185 independent reflections
Radiation source: sealed tube4601 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
T = 293(2) Kθmax = 25.0º
[var phi] & ω scansθmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −18→18
Tmin = 0.903, Tmax = 0.938k = −15→15
32977 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.105  w = 1/[σ2(Fo2) + (0.0839P)2 + 0.3838P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
5185 reflectionsΔρmax = 0.30 e Å3
451 parametersΔρmin = −0.44 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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*/Ueq
Co10.302202 (16)0.138211 (16)0.366964 (15)0.02739 (11)
O10.40452 (10)0.12832 (10)0.50951 (9)0.0376 (3)
O20.43227 (10)0.09578 (13)0.66013 (10)0.0538 (4)
O30.10352 (10)−0.00194 (13)0.60522 (10)0.0557 (4)
O40.07356 (9)0.08288 (12)0.31027 (9)0.0472 (4)
O50.98177 (15)0.12594 (16)0.76679 (18)0.0891 (7)
H330.95310.07010.75120.107*
H340.93880.16830.75800.107*
O60.90804 (17)0.18193 (17)0.28686 (18)0.1009 (8)
H350.94910.15180.27590.121*
H360.89460.13430.31450.121*
N10.22079 (10)0.09749 (11)0.43806 (10)0.0287 (3)
N20.09212 (11)0.04177 (12)0.45940 (11)0.0354 (4)
H20.03430.03050.43290.042*
N30.28705 (10)0.29594 (11)0.36494 (10)0.0299 (3)
N40.42213 (10)0.18951 (11)0.35070 (10)0.0299 (3)
N50.45316 (12)0.60117 (12)0.37989 (12)0.0406 (4)
N60.60438 (11)0.48810 (13)0.38628 (11)0.0398 (4)
N70.30777 (10)−0.01439 (11)0.33132 (10)0.0311 (3)
N80.21162 (11)0.13331 (10)0.21056 (11)0.0303 (3)
N90.17387 (14)−0.25488 (13)0.07249 (12)0.0474 (4)
N100.08181 (13)−0.09711 (13)−0.05752 (12)0.0460 (4)
C10.37945 (13)0.10401 (14)0.57318 (12)0.0337 (4)
C20.27470 (12)0.08264 (12)0.53502 (12)0.0295 (4)
C30.24123 (13)0.04902 (14)0.59542 (13)0.0360 (4)
H3A0.28200.04020.66100.043*
C40.14344 (13)0.02734 (15)0.55768 (13)0.0370 (4)
C50.12786 (13)0.07517 (13)0.39814 (12)0.0317 (4)
C60.21428 (14)0.34805 (14)0.36155 (14)0.0353 (4)
H60.16300.31330.35990.042*
C70.21152 (14)0.45158 (15)0.36044 (14)0.0395 (4)
H70.15840.48510.35560.047*
C80.28830 (14)0.50429 (15)0.36655 (13)0.0363 (4)
H80.28880.57380.36850.044*
C90.36554 (13)0.45180 (13)0.36978 (12)0.0289 (4)
C100.45001 (12)0.50074 (13)0.37630 (12)0.0309 (4)
C110.53149 (17)0.64312 (15)0.38635 (16)0.0468 (5)
H110.53650.71240.38830.056*
C120.60592 (15)0.58649 (16)0.39021 (15)0.0456 (5)
H120.65950.61950.39590.055*
C130.52507 (13)0.44397 (14)0.37875 (12)0.0310 (4)
C140.51799 (13)0.33593 (14)0.37159 (12)0.0305 (4)
C150.58863 (13)0.27483 (16)0.37097 (14)0.0390 (4)
H150.64490.30290.37820.047*
C160.57528 (14)0.17395 (16)0.35985 (15)0.0419 (5)
H160.62220.13270.35970.050*
C170.49038 (14)0.13382 (14)0.34878 (14)0.0351 (4)
H170.48090.06520.33970.042*
C180.43614 (12)0.28890 (13)0.36294 (11)0.0266 (4)
C190.36096 (12)0.34745 (13)0.36641 (12)0.0270 (4)
C200.35704 (15)−0.08618 (14)0.39335 (14)0.0406 (5)
H200.3975−0.06880.45720.049*
C210.35049 (16)−0.18542 (15)0.36665 (15)0.0453 (5)
H210.3856−0.23360.41220.054*
C220.29230 (14)−0.21251 (14)0.27315 (14)0.0382 (4)
H220.2871−0.27920.25460.046*
C230.24054 (13)−0.13879 (12)0.20537 (13)0.0320 (4)
C240.18141 (14)−0.15951 (14)0.10363 (15)0.0345 (4)
C250.11973 (18)−0.26838 (17)−0.02203 (16)0.0560 (6)
H250.1120−0.3330−0.04660.067*
C260.07401 (19)−0.19040 (18)−0.08593 (16)0.0558 (6)
H260.0366−0.2050−0.15120.067*
C270.13568 (13)−0.08080 (14)0.03829 (13)0.0343 (4)
C280.14542 (12)0.02137 (14)0.07340 (12)0.0323 (4)
C290.10276 (14)0.10256 (15)0.01198 (14)0.0393 (4)
H290.06600.0928−0.05430.047*
C300.11575 (15)0.19611 (16)0.05054 (14)0.0441 (5)
H300.08870.25110.01060.053*
C310.16973 (14)0.20886 (14)0.15002 (13)0.0391 (4)
H310.17690.27310.17540.047*
C320.20028 (12)0.04064 (13)0.17205 (12)0.0276 (4)
C330.25063 (12)−0.04016 (13)0.23834 (12)0.0276 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.03091 (17)0.02377 (17)0.02886 (16)−0.00288 (9)0.01500 (12)−0.00119 (8)
O10.0316 (7)0.0471 (8)0.0316 (7)−0.0091 (6)0.0124 (6)−0.0019 (5)
O20.0407 (8)0.0803 (12)0.0311 (7)−0.0083 (8)0.0088 (6)0.0007 (7)
O30.0465 (9)0.0841 (12)0.0447 (8)−0.0048 (8)0.0280 (7)0.0161 (8)
O40.0330 (7)0.0733 (11)0.0317 (7)−0.0048 (7)0.0118 (6)0.0063 (7)
O50.0666 (13)0.0695 (13)0.1107 (18)−0.0005 (10)0.0236 (12)0.0099 (11)
O60.1180 (18)0.0916 (15)0.145 (2)0.0530 (14)0.1050 (17)0.0658 (15)
N10.0301 (8)0.0286 (7)0.0285 (7)−0.0021 (6)0.0143 (6)−0.0001 (6)
N20.0299 (8)0.0425 (9)0.0360 (8)−0.0033 (7)0.0172 (7)0.0031 (7)
N30.0305 (8)0.0281 (8)0.0338 (8)−0.0039 (6)0.0173 (6)−0.0042 (6)
N40.0339 (8)0.0277 (8)0.0309 (7)0.0013 (6)0.0173 (6)0.0013 (6)
N50.0516 (10)0.0265 (8)0.0447 (9)−0.0061 (7)0.0233 (8)−0.0001 (7)
N60.0373 (9)0.0448 (10)0.0393 (9)−0.0107 (7)0.0193 (7)−0.0002 (7)
N70.0358 (8)0.0259 (7)0.0305 (8)0.0013 (6)0.0145 (6)0.0006 (6)
N80.0349 (9)0.0254 (8)0.0308 (8)−0.0022 (6)0.0155 (7)0.0006 (6)
N90.0634 (11)0.0342 (9)0.0505 (10)−0.0090 (8)0.0314 (9)−0.0114 (8)
N100.0582 (11)0.0467 (10)0.0352 (9)−0.0150 (9)0.0233 (8)−0.0078 (7)
C10.0361 (10)0.0321 (9)0.0296 (9)−0.0044 (8)0.0123 (8)−0.0037 (7)
C20.0339 (9)0.0258 (9)0.0289 (8)−0.0007 (7)0.0146 (7)−0.0022 (7)
C30.0391 (11)0.0397 (10)0.0288 (9)−0.0008 (8)0.0155 (8)0.0013 (8)
C40.0420 (11)0.0369 (10)0.0380 (10)−0.0006 (8)0.0235 (9)0.0038 (8)
C50.0336 (10)0.0312 (9)0.0328 (9)−0.0005 (8)0.0173 (8)0.0013 (7)
C60.0322 (10)0.0357 (10)0.0440 (11)−0.0016 (8)0.0226 (9)−0.0033 (8)
C70.0389 (11)0.0366 (10)0.0487 (11)0.0072 (8)0.0251 (9)−0.0003 (8)
C80.0435 (11)0.0275 (10)0.0411 (11)0.0043 (8)0.0222 (9)−0.0002 (7)
C90.0351 (10)0.0264 (9)0.0265 (8)−0.0009 (7)0.0154 (7)−0.0009 (7)
C100.0387 (10)0.0279 (9)0.0255 (8)−0.0049 (7)0.0143 (7)−0.0003 (7)
C110.0582 (14)0.0322 (11)0.0499 (12)−0.0155 (9)0.0251 (11)−0.0023 (8)
C120.0473 (12)0.0467 (13)0.0448 (11)−0.0188 (10)0.0228 (9)−0.0017 (9)
C130.0345 (10)0.0338 (10)0.0250 (8)−0.0063 (7)0.0141 (7)−0.0001 (7)
C140.0313 (9)0.0361 (10)0.0266 (8)0.0006 (8)0.0154 (7)0.0048 (7)
C150.0339 (10)0.0451 (12)0.0455 (11)0.0006 (8)0.0246 (9)0.0044 (9)
C160.0404 (11)0.0441 (12)0.0510 (11)0.0115 (9)0.0294 (9)0.0059 (9)
C170.0426 (11)0.0308 (10)0.0372 (10)0.0060 (8)0.0229 (9)0.0009 (7)
C180.0307 (9)0.0268 (9)0.0244 (8)−0.0003 (7)0.0144 (7)0.0007 (6)
C190.0306 (9)0.0281 (9)0.0228 (8)−0.0005 (7)0.0129 (7)0.0008 (6)
C200.0464 (12)0.0337 (10)0.0348 (10)0.0060 (9)0.0129 (8)0.0030 (8)
C210.0561 (13)0.0311 (10)0.0461 (12)0.0106 (9)0.0214 (10)0.0091 (9)
C220.0466 (11)0.0245 (9)0.0466 (11)0.0021 (8)0.0242 (9)−0.0001 (8)
C230.0353 (10)0.0283 (10)0.0387 (10)−0.0041 (7)0.0224 (9)−0.0034 (7)
C240.0389 (10)0.0335 (10)0.0393 (10)−0.0085 (8)0.0250 (8)−0.0079 (8)
C250.0813 (17)0.0403 (12)0.0524 (13)−0.0186 (12)0.0361 (12)−0.0187 (10)
C260.0767 (16)0.0548 (14)0.0397 (11)−0.0248 (12)0.0301 (11)−0.0182 (10)
C270.0387 (10)0.0370 (10)0.0328 (9)−0.0106 (8)0.0212 (8)−0.0068 (8)
C280.0325 (10)0.0343 (10)0.0335 (9)−0.0047 (7)0.0182 (8)−0.0010 (7)
C290.0408 (11)0.0436 (11)0.0301 (9)−0.0028 (9)0.0135 (8)0.0015 (8)
C300.0506 (12)0.0379 (11)0.0379 (10)0.0045 (9)0.0155 (9)0.0104 (8)
C310.0507 (12)0.0277 (9)0.0364 (10)0.0000 (8)0.0180 (9)0.0015 (8)
C320.0292 (9)0.0272 (9)0.0296 (8)−0.0035 (7)0.0164 (7)−0.0015 (7)
C330.0287 (9)0.0271 (9)0.0326 (9)−0.0012 (7)0.0188 (7)−0.0004 (7)

Geometric parameters (Å, °)

Co1—O12.0622 (13)C7—C81.378 (3)
Co1—N32.1223 (15)C7—H70.9300
Co1—N72.1280 (15)C8—C91.398 (3)
Co1—N12.1299 (14)C8—H80.9300
Co1—N42.1542 (15)C9—C191.397 (2)
Co1—N82.1827 (15)C9—C101.459 (2)
O1—C11.271 (2)C10—C131.403 (3)
O2—C11.224 (2)C11—C121.386 (3)
O3—C41.242 (2)C11—H110.9300
O4—C51.239 (2)C12—H120.9300
O5—H330.8499C13—C141.450 (3)
O5—H340.8500C14—C151.395 (3)
O6—H350.8512C14—C181.398 (2)
O6—H360.8494C15—C161.365 (3)
N1—C51.349 (2)C15—H150.9300
N1—C21.362 (2)C16—C171.391 (3)
N2—C41.374 (2)C16—H160.9300
N2—C51.392 (2)C17—H170.9300
N2—H20.8321C18—C191.454 (2)
N3—C61.334 (2)C20—C211.380 (3)
N3—C191.356 (2)C20—H200.9300
N4—C171.331 (2)C21—C221.364 (3)
N4—C181.347 (2)C21—H210.9300
N5—C111.330 (3)C22—C231.400 (3)
N5—C101.345 (2)C22—H220.9300
N6—C121.317 (3)C23—C331.398 (2)
N6—C131.351 (2)C23—C241.446 (3)
N7—C201.330 (2)C24—C271.410 (3)
N7—C331.350 (2)C25—C261.392 (3)
N8—C311.332 (2)C25—H250.9300
N8—C321.352 (2)C26—H260.9300
N9—C251.329 (3)C27—C281.453 (3)
N9—C241.350 (2)C28—C321.395 (2)
N10—C261.310 (3)C28—C291.398 (3)
N10—C271.351 (2)C29—C301.362 (3)
C1—C21.519 (3)C29—H290.9300
C2—C31.355 (2)C30—C311.391 (3)
C3—C41.419 (3)C30—H300.9300
C3—H3A0.9300C31—H310.9300
C6—C71.385 (3)C32—C331.453 (2)
C6—H60.9300
O1—Co1—N396.18 (5)N5—C11—C12121.89 (18)
O1—Co1—N796.39 (5)N5—C11—H11119.1
N3—Co1—N7165.47 (5)C12—C11—H11119.1
O1—Co1—N178.09 (5)N6—C12—C11123.17 (19)
N3—Co1—N199.75 (5)N6—C12—H12118.4
N7—Co1—N189.95 (6)C11—C12—H12118.4
O1—Co1—N480.99 (5)N6—C13—C10121.24 (17)
N3—Co1—N477.45 (5)N6—C13—C14118.61 (16)
N7—Co1—N497.38 (6)C10—C13—C14120.15 (15)
N1—Co1—N4158.47 (5)C15—C14—C18117.16 (17)
O1—Co1—N8169.75 (6)C15—C14—C13123.36 (16)
N3—Co1—N890.07 (5)C18—C14—C13119.47 (16)
N7—Co1—N876.48 (5)C16—C15—C14120.07 (18)
N1—Co1—N8108.90 (6)C16—C15—H15120.0
N4—Co1—N892.51 (6)C14—C15—H15120.0
C1—O1—Co1118.54 (12)C15—C16—C17118.88 (18)
H33—O5—H34104.6C15—C16—H16120.6
H35—O6—H3698.3C17—C16—H16120.6
C5—N1—C2118.28 (14)N4—C17—C16122.72 (17)
C5—N1—Co1128.40 (11)N4—C17—H17118.6
C2—N1—Co1112.90 (11)C16—C17—H17118.6
C4—N2—C5125.88 (16)N4—C18—C14122.96 (16)
C4—N2—H2118.6N4—C18—C19116.83 (15)
C5—N2—H2115.5C14—C18—C19120.21 (16)
C6—N3—C19117.94 (15)N3—C19—C9122.54 (16)
C6—N3—Co1127.68 (12)N3—C19—C18116.80 (15)
C19—N3—Co1114.38 (11)C9—C19—C18120.65 (16)
C17—N4—C18118.16 (16)N7—C20—C21122.59 (18)
C17—N4—Co1127.17 (12)N7—C20—H20118.7
C18—N4—Co1113.32 (11)C21—C20—H20118.7
C11—N5—C10116.12 (17)C22—C21—C20119.74 (18)
C12—N6—C13115.93 (18)C22—C21—H21120.1
C20—N7—C33118.21 (15)C20—C21—H21120.1
C20—N7—Co1125.81 (12)C21—C22—C23119.32 (17)
C33—N7—Co1115.82 (11)C21—C22—H22120.3
C31—N8—C32117.49 (15)C23—C22—H22120.3
C31—N8—Co1128.53 (12)C33—C23—C22117.41 (17)
C32—N8—Co1113.94 (11)C33—C23—C24119.27 (16)
C25—N9—C24115.47 (19)C22—C23—C24123.26 (16)
C26—N10—C27116.04 (19)N9—C24—C27121.07 (18)
O2—C1—O1125.55 (18)N9—C24—C23118.61 (18)
O2—C1—C2119.03 (17)C27—C24—C23120.28 (17)
O1—C1—C2115.41 (15)N9—C25—C26123.1 (2)
C3—C2—N1124.61 (16)N9—C25—H25118.4
C3—C2—C1120.41 (16)C26—C25—H25118.4
N1—C2—C1114.96 (15)N10—C26—C25122.4 (2)
C2—C3—C4119.40 (16)N10—C26—H26118.8
C2—C3—H3A120.3C25—C26—H26118.8
C4—C3—H3A120.3N10—C27—C24121.89 (18)
O3—C4—N2120.15 (17)N10—C27—C28118.03 (17)
O3—C4—C3125.87 (18)C24—C27—C28120.08 (16)
N2—C4—C3113.98 (15)C32—C28—C29117.91 (17)
O4—C5—N1123.22 (16)C32—C28—C27119.42 (16)
O4—C5—N2118.98 (16)C29—C28—C27122.67 (16)
N1—C5—N2117.80 (15)C30—C29—C28119.07 (17)
N3—C6—C7123.02 (17)C30—C29—H29120.5
N3—C6—H6118.5C28—C29—H29120.5
C7—C6—H6118.5C29—C30—C31119.54 (18)
C8—C7—C6119.25 (18)C29—C30—H30120.2
C8—C7—H7120.4C31—C30—H30120.2
C6—C7—H7120.4N8—C31—C30122.98 (18)
C7—C8—C9119.05 (18)N8—C31—H31118.5
C7—C8—H8120.5C30—C31—H31118.5
C9—C8—H8120.5N8—C32—C28122.98 (16)
C19—C9—C8118.06 (17)N8—C32—C33116.77 (15)
C19—C9—C10118.78 (16)C28—C32—C33120.22 (16)
C8—C9—C10123.16 (17)N7—C33—C23122.72 (16)
N5—C10—C13121.65 (16)N7—C33—C32116.64 (15)
N5—C10—C9117.83 (16)C23—C33—C32120.63 (16)
C13—C10—C9120.52 (16)
N3—Co1—O1—C199.21 (14)C13—N6—C12—C11−0.4 (3)
N7—Co1—O1—C1−88.09 (14)N5—C11—C12—N61.1 (3)
N1—Co1—O1—C10.51 (13)C12—N6—C13—C10−0.6 (2)
N4—Co1—O1—C1175.42 (14)C12—N6—C13—C14178.44 (16)
N8—Co1—O1—C1−133.4 (3)N5—C10—C13—N61.0 (3)
O1—Co1—N1—C5−174.59 (16)C9—C10—C13—N6−178.97 (15)
N3—Co1—N1—C591.09 (15)N5—C10—C13—C14−178.01 (16)
N7—Co1—N1—C5−78.04 (15)C9—C10—C13—C142.0 (2)
N4—Co1—N1—C5171.59 (15)N6—C13—C14—C15−0.7 (3)
N8—Co1—N1—C5−2.37 (16)C10—C13—C14—C15178.29 (16)
O1—Co1—N1—C2−2.29 (11)N6—C13—C14—C18−179.48 (15)
N3—Co1—N1—C2−96.62 (12)C10—C13—C14—C18−0.4 (2)
N7—Co1—N1—C294.25 (12)C18—C14—C15—C161.6 (3)
N4—Co1—N1—C2−16.1 (2)C13—C14—C15—C16−177.18 (17)
N8—Co1—N1—C2169.93 (11)C14—C15—C16—C170.3 (3)
O1—Co1—N3—C6−108.60 (15)C18—N4—C17—C160.7 (3)
N7—Co1—N3—C6101.6 (2)Co1—N4—C17—C16−165.11 (14)
N1—Co1—N3—C6−29.67 (15)C15—C16—C17—N4−1.5 (3)
N4—Co1—N3—C6172.09 (15)C17—N4—C18—C141.4 (2)
N8—Co1—N3—C679.53 (15)Co1—N4—C18—C14169.10 (12)
O1—Co1—N3—C1972.07 (12)C17—N4—C18—C19−178.96 (14)
N7—Co1—N3—C19−77.7 (3)Co1—N4—C18—C19−11.25 (18)
N1—Co1—N3—C19150.99 (11)C15—C14—C18—N4−2.5 (2)
N4—Co1—N3—C19−7.25 (11)C13—C14—C18—N4176.31 (15)
N8—Co1—N3—C19−99.80 (12)C15—C14—C18—C19177.85 (15)
O1—Co1—N4—C1777.88 (15)C13—C14—C18—C19−3.3 (2)
N3—Co1—N4—C17176.33 (15)C6—N3—C19—C93.5 (2)
N7—Co1—N4—C17−17.47 (15)Co1—N3—C19—C9−177.07 (12)
N1—Co1—N4—C1791.6 (2)C6—N3—C19—C18−175.63 (15)
N8—Co1—N4—C17−94.15 (15)Co1—N3—C19—C183.77 (18)
O1—Co1—N4—C18−88.50 (12)C8—C9—C19—N3−3.3 (2)
N3—Co1—N4—C189.96 (11)C10—C9—C19—N3176.82 (15)
N7—Co1—N4—C18176.16 (11)C8—C9—C19—C18175.84 (15)
N1—Co1—N4—C18−74.8 (2)C10—C9—C19—C18−4.1 (2)
N8—Co1—N4—C1899.47 (12)N4—C18—C19—N35.2 (2)
O1—Co1—N7—C207.01 (17)C14—C18—C19—N3−175.14 (14)
N3—Co1—N7—C20156.8 (2)N4—C18—C19—C9−173.98 (15)
N1—Co1—N7—C20−71.00 (16)C14—C18—C19—C95.7 (2)
N4—Co1—N7—C2088.70 (16)C33—N7—C20—C21−1.2 (3)
N8—Co1—N7—C20179.53 (17)Co1—N7—C20—C21173.85 (15)
O1—Co1—N7—C33−177.80 (12)N7—C20—C21—C220.6 (3)
N3—Co1—N7—C33−28.0 (3)C20—C21—C22—C230.5 (3)
N1—Co1—N7—C33104.20 (12)C21—C22—C23—C33−0.9 (3)
N4—Co1—N7—C33−96.10 (12)C21—C22—C23—C24176.28 (19)
N8—Co1—N7—C33−5.28 (12)C25—N9—C24—C27−1.2 (3)
O1—Co1—N8—C31−127.7 (3)C25—N9—C24—C23−178.90 (18)
N3—Co1—N8—C310.04 (17)C33—C23—C24—N9178.66 (17)
N7—Co1—N8—C31−174.40 (18)C22—C23—C24—N91.5 (3)
N1—Co1—N8—C31100.38 (17)C33—C23—C24—C271.0 (3)
N4—Co1—N8—C31−77.41 (17)C22—C23—C24—C27−176.18 (18)
O1—Co1—N8—C3250.1 (3)C24—N9—C25—C260.6 (3)
N3—Co1—N8—C32177.92 (12)C27—N10—C26—C25−1.2 (3)
N7—Co1—N8—C323.48 (12)N9—C25—C26—N100.7 (4)
N1—Co1—N8—C32−81.74 (13)C26—N10—C27—C240.5 (3)
N4—Co1—N8—C32100.47 (12)C26—N10—C27—C28−179.22 (18)
Co1—O1—C1—O2−179.64 (16)N9—C24—C27—N100.7 (3)
Co1—O1—C1—C21.2 (2)C23—C24—C27—N10178.37 (17)
C5—N1—C2—C3−1.7 (3)N9—C24—C27—C28−179.52 (17)
Co1—N1—C2—C3−174.80 (15)C23—C24—C27—C28−1.9 (3)
C5—N1—C2—C1176.70 (15)N10—C27—C28—C32179.74 (16)
Co1—N1—C2—C13.55 (18)C24—C27—C28—C320.0 (3)
O2—C1—C2—C3−4.0 (3)N10—C27—C28—C29−1.1 (3)
O1—C1—C2—C3175.16 (17)C24—C27—C28—C29179.19 (18)
O2—C1—C2—N1177.54 (17)C32—C28—C29—C30−0.4 (3)
O1—C1—C2—N1−3.3 (2)C27—C28—C29—C30−179.66 (18)
N1—C2—C3—C4−0.3 (3)C28—C29—C30—C31−1.0 (3)
C1—C2—C3—C4−178.53 (17)C32—N8—C31—C300.0 (3)
C5—N2—C4—O3179.30 (19)Co1—N8—C31—C30177.86 (15)
C5—N2—C4—C3−0.5 (3)C29—C30—C31—N81.3 (3)
C2—C3—C4—O3−178.5 (2)C31—N8—C32—C28−1.6 (3)
C2—C3—C4—N21.3 (3)Co1—N8—C32—C28−179.74 (13)
C2—N1—C5—O4−177.54 (17)C31—N8—C32—C33176.74 (16)
Co1—N1—C5—O4−5.6 (3)Co1—N8—C32—C33−1.39 (19)
C2—N1—C5—N22.3 (2)C29—C28—C32—N81.8 (3)
Co1—N1—C5—N2174.28 (12)C27—C28—C32—N8−178.94 (16)
C4—N2—C5—O4178.55 (18)C29—C28—C32—C33−176.47 (16)
C4—N2—C5—N1−1.3 (3)C27—C28—C32—C332.8 (2)
C19—N3—C6—C7−0.6 (3)C20—N7—C33—C230.8 (3)
Co1—N3—C6—C7−179.95 (14)Co1—N7—C33—C23−174.80 (13)
N3—C6—C7—C8−2.4 (3)C20—N7—C33—C32−178.09 (16)
C6—C7—C8—C92.5 (3)Co1—N7—C33—C326.33 (19)
C7—C8—C9—C190.1 (2)C22—C23—C33—N70.3 (3)
C7—C8—C9—C10−179.97 (16)C24—C23—C33—N7−177.03 (16)
C11—N5—C10—C13−0.3 (3)C22—C23—C33—C32179.12 (16)
C11—N5—C10—C9179.64 (16)C24—C23—C33—C321.8 (3)
C19—C9—C10—N5−179.72 (15)N8—C32—C33—N7−3.2 (2)
C8—C9—C10—N50.4 (2)C28—C32—C33—N7175.18 (15)
C19—C9—C10—C130.3 (2)N8—C32—C33—C23177.88 (15)
C8—C9—C10—C13−179.64 (16)C28—C32—C33—C23−3.7 (2)
C10—N5—C11—C12−0.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H33···O4i0.852.223.007 (3)155
O5—H34···O6ii0.852.162.903 (3)146
O6—H35···O4iii0.852.022.822 (2)156
O6—H36···O3i0.852.162.990 (2)166
N2—H2···O3iv0.832.032.850 (2)169

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FI2050).

References

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  • Lalioti, N., Raptopoulou, C. P., Terzis, A., Panagiotopoulos, A., Perlepes, S. P. & Manessi-Zoupa, E. (1998). J. Chem. Soc. Dalton Trans. pp. 1335–1340.
  • Lieberman, I., Komberg, A. & Simms, E. S. (1955). J. Biol. Chem.215, 403–415. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Sheldrick, G. M. (1997b). SHELXTL Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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