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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m851.
Published online 2009 July 1. doi:  10.1107/S1600536809024234
PMCID: PMC2977374

Bis[1,3-bis­(benzimidazol-2-yl)-2-oxa­propane]cobalt(II) dipicrate acetonitrile tris­olvate

Abstract

In the title compound, [Co(C16H14N4O)2](C6H2N3O7)2·3CH3CN, the CoII ion is located on a crystallographic twofold rotation axis and is coordinated in a slightly distorted tetra­hedral environment by four N atoms from the two bidentate N-heterocycles. The crystal structure is stabilized by inter­molecular N—H(...)O and N—H(...)N hydrogen bonds. One of the acetonitrile solvent mol­ecules also lies on a twofold rotation axis.

Related literature

For the crystal structures of related dipicrate metal complexes with 1,3-bis­(1-benzyl-1H-benzimidazol-2-yl)-2-oxapropane ligands, see: Wu, Yun, Li, Wang & Huang (2009 [triangle]); Wu, Yun, Li, Tao & Wang (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m851-scheme1.jpg

Experimental

Crystal data

  • [Co(C16H14N4O)2](C6H2N3O7)2·3C2H3N
  • M r = 1194.93
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m851-efi2.jpg
  • a = 11.4114 (3) Å
  • b = 9.9303 (2) Å
  • c = 25.1442 (6) Å
  • β = 111.164 (1)°
  • V = 2657.12 (11) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.41 mm−1
  • T = 153 K
  • 0.28 × 0.25 × 0.17 mm

Data collection

  • Rigaku R-AXIS Spider diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.894, T max = 0.933
  • 25278 measured reflections
  • 6093 independent reflections
  • 5418 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.087
  • S = 1.04
  • 6093 reflections
  • 392 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.45 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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 global, I. DOI: 10.1107/S1600536809024234/lh2846sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024234/lh2846Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support and a grant from the ‘Qing Lan’ Talent Engineering Funds and the Students’ Science and Technology Innovation Funds (grant No. DXS2008–040,041) of Lanzhou Jiaotong University. A grant from ‘Long Yuan Qing Nian’ of Gansu Province is also acknowledged.

supplementary crystallographic information

Comment

The asymmetric unit of the title compound consists of half a discrete di[1,3-bis(benzimidazol-2-yl)-2-oxopropane] cobalt(II) cation, one picrate anion and 1.5 molecules of acetonitrile; the formula unit is generated by a twofold rotation axis. The cation is shown in Fig. 1. The CoII ion is four-coordinate with a N4 ligand set. The (1,3-bis(benzimidazol-2-yl)-2-oxopropane) ligand acts as a bidentate donor. The coordination geometry of the CoII may be best described as slightly distorted tetrahedral. This geometry is assumed by the CoII to relieve the steric crowding. The crystal structure is stabilized by intermolecular N—H···O and N—H···N hydrogen bonds. Additional stabilization is provided by weak intermolecular C-H···O hydrogen bonds (Fig. 2).

Experimental

To a stirred solution of 1,3-bis(benzimidazol-2-yl)-2-oxopropane (0.139 g, 0.5 mmol) in hot MeOH (15 ml) was added Co(C6H2N3O7)2 (0.129 g, 0.25 mmol) in MeOH (5 ml). A red crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH and absolute Et2O, and dried in vacuo. The dried precipitate was dissolved in acetonitrile to form a red solution that was allowed to evaporate at room temperature. Red crystals suitable for X-ray diffraction studies were obtained after three days at room temperature. Yield, 0.106 g (66%). (found: C, 50.20; H, 3.51; N,19.94. Calcd. for C50H41N17O16Co: C, 50.26; H, 3.46; N, 19.93)

Refinement

All H atoms were found in difference electron maps and were subsequently included in a riding-model approximation with C—H distances ranging from 0.95 to 0.99 Å and Uiso(H) = 1.2 Ueq of the carrier atom. The H atoms bonded to N atoms were refined independently with the distance constraint of N—H 0.858 (9) Å.

Figures

Fig. 1.
Molecular structure and atom numbering for the cation of the title compound. Hydrogen atoms have been omitted for clarity and the displacement ellipsoids are shown at the 30% probability level [symmetry code: (A) -x+1, y, -z+3/2].
Fig. 2.
Part of the crystal structure with hydrogen bonds shown as dashed lines.

Crystal data

[Co(C16H14N4O)2](C6H2N3O7)2·3C2H3NF(000) = 1230
Mr = 1194.93Dx = 1.494 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 7749 reflections
a = 11.4114 (3) Åθ = 3.2–27.5°
b = 9.9303 (2) ŵ = 0.41 mm1
c = 25.1442 (6) ÅT = 153 K
β = 111.164 (1)°Block, red
V = 2657.12 (11) Å30.28 × 0.25 × 0.17 mm
Z = 2

Data collection

Rigaku R-AXIS Spider diffractometer6093 independent reflections
Radiation source: fine-focus sealed tube5418 reflections with I > 2σ(I)
graphiteRint = 0.021
[var phi] and ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −14→14
Tmin = 0.894, Tmax = 0.933k = −12→12
25278 measured reflectionsl = −32→32

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087w = 1/[σ2(Fo2) + (0.0487P)2 + 0.9118P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
6093 reflectionsΔρmax = 0.45 e Å3
392 parametersΔρmin = −0.30 e Å3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0036 (5)

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)
Co0.50000.36301 (2)0.75000.01700 (8)
O10.67337 (8)0.24981 (9)0.71220 (4)0.02259 (19)
O20.74591 (13)0.49084 (15)0.46620 (6)0.0583 (4)
O30.54824 (12)0.47322 (11)0.41556 (5)0.0409 (3)
O40.25535 (11)0.76959 (16)0.44436 (6)0.0567 (4)
O50.29928 (11)0.88294 (12)0.52194 (5)0.0428 (3)
O60.54003 (9)0.96666 (10)0.56756 (4)0.0292 (2)
O70.78254 (12)0.91568 (16)0.63960 (5)0.0522 (3)
O80.88585 (11)0.89860 (13)0.58266 (5)0.0420 (3)
N10.41234 (10)0.25020 (10)0.67914 (4)0.0200 (2)
N20.39034 (10)0.10735 (11)0.60795 (4)0.0202 (2)
N30.62918 (10)0.49981 (11)0.74562 (4)0.0195 (2)
N40.77113 (11)0.58828 (12)0.71442 (5)0.0260 (2)
N50.63674 (13)0.52737 (13)0.45326 (5)0.0342 (3)
N60.33090 (11)0.81256 (13)0.48951 (5)0.0309 (3)
N70.79113 (12)0.88240 (13)0.59422 (5)0.0332 (3)
N80.93174 (15)0.59702 (16)0.64743 (6)0.0452 (4)
N91.00000.3626 (2)0.75000.0471 (5)
C10.28403 (12)0.23999 (12)0.64561 (5)0.0196 (2)
C20.17845 (12)0.29913 (14)0.65151 (5)0.0252 (3)
H20.18600.36040.68160.030*
C30.06220 (13)0.26482 (15)0.61173 (6)0.0282 (3)
H3−0.01130.30290.61500.034*
C40.04975 (13)0.17528 (15)0.56674 (6)0.0278 (3)
H4−0.03170.15460.54020.033*
C50.15352 (13)0.11673 (14)0.56030 (6)0.0249 (3)
H50.14580.05680.52980.030*
C60.26998 (12)0.14996 (12)0.60080 (5)0.0194 (2)
C70.47004 (12)0.16761 (12)0.65481 (5)0.0197 (2)
C80.60830 (12)0.13872 (13)0.67854 (6)0.0252 (3)
H8A0.62440.05640.70230.030*
H8B0.63910.12310.64690.030*
C90.68619 (12)0.35957 (13)0.67806 (5)0.0222 (3)
H9A0.61210.36500.64220.027*
H9B0.76240.34810.66840.027*
C100.69630 (11)0.48306 (13)0.71274 (5)0.0201 (2)
C110.75372 (13)0.68185 (14)0.75169 (6)0.0267 (3)
C120.80865 (17)0.80687 (16)0.77019 (7)0.0396 (4)
H120.86850.84460.75620.047*
C130.77203 (19)0.87304 (16)0.80967 (8)0.0450 (4)
H130.80710.95880.82320.054*
C140.68394 (17)0.81668 (16)0.83043 (7)0.0393 (4)
H140.66120.86530.85780.047*
C150.62941 (14)0.69269 (15)0.81217 (6)0.0293 (3)
H150.57020.65490.82650.035*
C160.66544 (13)0.62542 (13)0.77169 (5)0.0221 (3)
C170.61070 (14)0.63884 (13)0.48431 (6)0.0262 (3)
C180.48772 (13)0.67268 (13)0.47497 (5)0.0238 (3)
H180.42080.62220.44890.029*
C190.46257 (13)0.78010 (13)0.50371 (5)0.0233 (3)
C200.55850 (13)0.86220 (13)0.54417 (5)0.0228 (3)
C210.68386 (13)0.81456 (14)0.55233 (6)0.0260 (3)
C220.70968 (14)0.71058 (15)0.52261 (6)0.0288 (3)
H220.79410.68780.52810.035*
C231.05744 (17)0.6226 (2)0.58074 (8)0.0495 (5)
H23A1.01270.57550.54490.059*
H23B1.14150.58370.59870.059*
H23C1.06480.71830.57300.059*
C240.98832 (15)0.60810 (18)0.61876 (7)0.0371 (4)
C251.00000.1051 (3)0.75000.0971 (16)
H25A1.06910.07220.78360.116*0.50
H25B1.01100.07220.71540.116*0.50
H25C0.91990.07220.75110.116*0.50
C261.00000.2497 (2)0.75000.0355 (5)
H2N0.4130 (16)0.0525 (15)0.5871 (7)0.037 (5)*
H4N0.8242 (14)0.5947 (19)0.6975 (7)0.041 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co0.01758 (12)0.01751 (13)0.01522 (12)0.0000.00511 (9)0.000
O10.0227 (5)0.0215 (4)0.0208 (4)−0.0016 (3)0.0046 (4)−0.0025 (3)
O20.0533 (8)0.0616 (9)0.0637 (8)0.0260 (7)0.0257 (7)−0.0152 (7)
O30.0612 (8)0.0328 (6)0.0310 (5)0.0086 (5)0.0194 (5)−0.0069 (5)
O40.0274 (6)0.0785 (10)0.0554 (8)−0.0016 (6)0.0044 (6)−0.0380 (7)
O50.0291 (6)0.0489 (7)0.0506 (7)0.0037 (5)0.0147 (5)−0.0249 (6)
O60.0275 (5)0.0275 (5)0.0321 (5)0.0021 (4)0.0102 (4)−0.0101 (4)
O70.0354 (6)0.0790 (10)0.0353 (6)0.0055 (6)0.0046 (5)−0.0223 (6)
O80.0292 (6)0.0469 (7)0.0486 (7)−0.0026 (5)0.0126 (5)0.0015 (5)
N10.0186 (5)0.0204 (5)0.0200 (5)0.0016 (4)0.0058 (4)−0.0023 (4)
N20.0214 (5)0.0189 (5)0.0203 (5)0.0001 (4)0.0075 (4)−0.0037 (4)
N30.0211 (5)0.0207 (5)0.0178 (5)−0.0001 (4)0.0082 (4)−0.0005 (4)
N40.0287 (6)0.0261 (6)0.0286 (6)−0.0045 (5)0.0170 (5)−0.0010 (5)
N50.0495 (8)0.0292 (6)0.0304 (6)0.0138 (6)0.0222 (6)0.0023 (5)
N60.0251 (6)0.0324 (6)0.0345 (6)0.0000 (5)0.0100 (5)−0.0109 (5)
N70.0271 (6)0.0361 (7)0.0327 (6)0.0065 (5)0.0061 (5)−0.0024 (5)
N80.0477 (9)0.0524 (9)0.0459 (8)0.0125 (7)0.0295 (7)0.0123 (7)
N90.0421 (12)0.0387 (12)0.0568 (13)0.0000.0132 (10)0.000
C10.0192 (6)0.0204 (6)0.0178 (5)−0.0006 (5)0.0052 (5)−0.0001 (4)
C20.0217 (6)0.0300 (7)0.0234 (6)0.0023 (5)0.0074 (5)−0.0052 (5)
C30.0199 (6)0.0351 (7)0.0289 (7)0.0021 (5)0.0080 (5)−0.0046 (6)
C40.0203 (6)0.0330 (7)0.0259 (6)−0.0026 (5)0.0035 (5)−0.0040 (6)
C50.0247 (7)0.0264 (6)0.0215 (6)−0.0022 (5)0.0059 (5)−0.0051 (5)
C60.0204 (6)0.0191 (6)0.0196 (5)−0.0003 (4)0.0082 (5)0.0008 (4)
C70.0212 (6)0.0167 (5)0.0209 (6)−0.0001 (5)0.0073 (5)−0.0009 (4)
C80.0206 (6)0.0220 (6)0.0294 (6)0.0019 (5)0.0049 (5)−0.0078 (5)
C90.0217 (6)0.0264 (7)0.0198 (6)0.0004 (5)0.0091 (5)−0.0015 (5)
C100.0189 (6)0.0239 (6)0.0179 (5)0.0011 (5)0.0073 (5)0.0026 (5)
C110.0299 (7)0.0246 (7)0.0280 (6)−0.0030 (5)0.0133 (6)−0.0004 (5)
C120.0469 (9)0.0293 (8)0.0490 (9)−0.0132 (7)0.0251 (8)−0.0049 (7)
C130.0582 (11)0.0270 (8)0.0540 (10)−0.0149 (7)0.0254 (9)−0.0139 (7)
C140.0509 (10)0.0305 (8)0.0415 (8)−0.0047 (7)0.0228 (8)−0.0134 (7)
C150.0347 (8)0.0284 (7)0.0283 (6)−0.0023 (6)0.0156 (6)−0.0056 (6)
C160.0240 (6)0.0213 (6)0.0211 (6)−0.0010 (5)0.0080 (5)−0.0001 (5)
C170.0380 (8)0.0225 (6)0.0229 (6)0.0085 (5)0.0168 (6)0.0030 (5)
C180.0335 (7)0.0202 (6)0.0203 (6)0.0012 (5)0.0130 (5)0.0008 (5)
C190.0259 (7)0.0229 (6)0.0229 (6)0.0037 (5)0.0111 (5)−0.0006 (5)
C200.0256 (7)0.0230 (6)0.0216 (6)0.0032 (5)0.0106 (5)0.0002 (5)
C210.0252 (7)0.0282 (7)0.0238 (6)0.0038 (5)0.0081 (5)0.0003 (5)
C220.0287 (7)0.0332 (7)0.0269 (6)0.0109 (6)0.0129 (6)0.0036 (6)
C230.0350 (9)0.0802 (14)0.0412 (9)0.0146 (9)0.0233 (8)0.0109 (9)
C240.0319 (8)0.0471 (9)0.0344 (8)0.0142 (7)0.0146 (7)0.0100 (7)
C250.109 (3)0.0309 (15)0.110 (3)0.000−0.011 (3)0.000
C260.0263 (10)0.0338 (12)0.0407 (11)0.0000.0052 (9)0.000

Geometric parameters (Å, °)

Co—N12.0355 (10)C4—H40.9500
Co—N1i2.0355 (10)C5—C61.3910 (18)
Co—N32.0367 (11)C5—H50.9500
Co—N3i2.0367 (11)C7—C81.4993 (18)
O1—C81.4250 (15)C8—H8A0.9900
O1—C91.4272 (16)C8—H8B0.9900
O2—N51.2234 (19)C9—C101.4849 (18)
O3—N51.2315 (18)C9—H9A0.9900
O4—N61.2278 (17)C9—H9B0.9900
O5—N61.2233 (16)C11—C121.393 (2)
O6—C201.2475 (16)C11—C161.3956 (19)
O7—N71.2255 (17)C12—C131.375 (2)
O8—N71.2270 (17)C12—H120.9500
N1—C71.3308 (16)C13—C141.405 (3)
N1—C11.4048 (16)C13—H130.9500
N2—C71.3416 (16)C14—C151.381 (2)
N2—C61.3855 (16)C14—H140.9500
N2—H2N0.858 (9)C15—C161.3977 (19)
N3—C101.3247 (15)C15—H150.9500
N3—C161.4004 (16)C17—C181.378 (2)
N4—C101.3404 (17)C17—C221.388 (2)
N4—C111.3840 (18)C18—C191.3756 (18)
N4—H4N0.858 (9)C18—H180.9500
N5—C171.4459 (17)C19—C201.4469 (19)
N6—C191.4497 (18)C20—C211.4492 (19)
N7—C211.4597 (19)C21—C221.368 (2)
N8—C241.133 (2)C22—H220.9500
N9—C261.121 (3)C23—C241.450 (2)
C1—C21.3956 (18)C23—H23A0.9800
C1—C61.4013 (17)C23—H23B0.9800
C2—C31.3850 (19)C23—H23C0.9800
C2—H20.9500C25—C261.436 (4)
C3—C41.405 (2)C25—H25A0.9800
C3—H30.9500C25—H25B0.9800
C4—C51.380 (2)C25—H25C0.9800
N1—Co—N1i113.22 (6)C10—C9—H9A110.5
N1—Co—N3117.15 (4)O1—C9—H9B110.5
N1i—Co—N3106.14 (4)C10—C9—H9B110.5
N1—Co—N3i106.13 (4)H9A—C9—H9B108.7
N1i—Co—N3i117.15 (4)N3—C10—N4112.81 (11)
N3—Co—N3i96.33 (6)N3—C10—C9122.03 (11)
C8—O1—C9112.25 (10)N4—C10—C9125.15 (11)
C7—N1—C1105.13 (10)N4—C11—C12131.85 (13)
C7—N1—Co124.97 (9)N4—C11—C16105.85 (12)
C1—N1—Co129.90 (8)C12—C11—C16122.27 (13)
C7—N2—C6107.67 (10)C13—C12—C11116.71 (15)
C7—N2—H2N124.2 (12)C13—C12—H12121.6
C6—N2—H2N128.2 (12)C11—C12—H12121.6
C10—N3—C16105.33 (10)C12—C13—C14121.49 (14)
C10—N3—Co122.88 (9)C12—C13—H13119.3
C16—N3—Co131.77 (8)C14—C13—H13119.3
C10—N4—C11107.41 (11)C15—C14—C13121.90 (14)
C10—N4—H4N126.7 (13)C15—C14—H14119.0
C11—N4—H4N125.8 (13)C13—C14—H14119.0
O2—N5—O3123.27 (13)C14—C15—C16116.89 (14)
O2—N5—C17118.13 (14)C14—C15—H15121.6
O3—N5—C17118.60 (13)C16—C15—H15121.6
O5—N6—O4122.50 (13)C11—C16—C15120.73 (13)
O5—N6—C19119.46 (12)C11—C16—N3108.58 (11)
O4—N6—C19118.03 (12)C15—C16—N3130.67 (12)
O7—N7—O8123.97 (14)C18—C17—C22121.11 (12)
O7—N7—C21117.91 (13)C18—C17—N5119.33 (13)
O8—N7—C21118.07 (12)C22—C17—N5119.56 (13)
C2—C1—C6120.09 (12)C19—C18—C17119.49 (13)
C2—C1—N1131.19 (11)C19—C18—H18120.3
C6—C1—N1108.69 (11)C17—C18—H18120.3
C3—C2—C1117.27 (12)C18—C19—C20123.90 (12)
C3—C2—H2121.4C18—C19—N6115.93 (12)
C1—C2—H2121.4C20—C19—N6120.12 (11)
C2—C3—C4121.95 (13)O6—C20—C19125.89 (12)
C2—C3—H3119.0O6—C20—C21122.06 (13)
C4—C3—H3119.0C19—C20—C21111.92 (11)
C5—C4—C3121.29 (12)C22—C21—C20124.43 (13)
C5—C4—H4119.4C22—C21—N7116.92 (13)
C3—C4—H4119.4C20—C21—N7118.64 (12)
C4—C5—C6116.58 (12)C21—C22—C17119.00 (13)
C4—C5—H5121.7C21—C22—H22120.5
C6—C5—H5121.7C17—C22—H22120.5
N2—C6—C5131.51 (12)C24—C23—H23A109.5
N2—C6—C1105.68 (11)C24—C23—H23B109.5
C5—C6—C1122.80 (12)H23A—C23—H23B109.5
N1—C7—N2112.80 (11)C24—C23—H23C109.5
N1—C7—C8124.00 (11)H23A—C23—H23C109.5
N2—C7—C8123.12 (11)H23B—C23—H23C109.5
O1—C8—C7109.64 (10)N8—C24—C23178.40 (18)
O1—C8—H8A109.7C26—C25—H25A109.5
C7—C8—H8A109.7C26—C25—H25B109.5
O1—C8—H8B109.7H25A—C25—H25B109.5
C7—C8—H8B109.7C26—C25—H25C109.5
H8A—C8—H8B108.2H25A—C25—H25C109.5
O1—C9—C10106.29 (10)H25B—C25—H25C109.5
O1—C9—H9A110.5N9—C26—C25180.000 (3)
N1i—Co—N1—C7−63.92 (10)O1—C9—C10—N4141.87 (12)
N3—Co—N1—C760.12 (11)C10—N4—C11—C12178.52 (17)
N3i—Co—N1—C7166.22 (10)C10—N4—C11—C160.22 (15)
N1i—Co—N1—C1116.01 (11)N4—C11—C12—C13−177.85 (17)
N3—Co—N1—C1−119.95 (10)C16—C11—C12—C130.2 (3)
N3i—Co—N1—C1−13.86 (11)C11—C12—C13—C140.3 (3)
N1—Co—N3—C10−29.43 (11)C12—C13—C14—C15−0.3 (3)
N1i—Co—N3—C1098.12 (10)C13—C14—C15—C16−0.3 (3)
N3i—Co—N3—C10−141.21 (11)N4—C11—C16—C15177.74 (13)
N1—Co—N3—C16148.33 (10)C12—C11—C16—C15−0.8 (2)
N1i—Co—N3—C16−84.11 (11)N4—C11—C16—N3−0.97 (15)
N3i—Co—N3—C1636.55 (10)C12—C11—C16—N3−179.47 (14)
C7—N1—C1—C2177.34 (14)C14—C15—C16—C110.8 (2)
Co—N1—C1—C2−2.6 (2)C14—C15—C16—N3179.14 (14)
C7—N1—C1—C6−0.67 (13)C10—N3—C16—C111.34 (14)
Co—N1—C1—C6179.40 (8)Co—N3—C16—C11−176.71 (9)
C6—C1—C2—C30.0 (2)C10—N3—C16—C15−177.19 (14)
N1—C1—C2—C3−177.80 (13)Co—N3—C16—C154.8 (2)
C1—C2—C3—C4−0.6 (2)O2—N5—C17—C18−172.99 (14)
C2—C3—C4—C50.3 (2)O3—N5—C17—C186.38 (19)
C3—C4—C5—C60.6 (2)O2—N5—C17—C227.5 (2)
C7—N2—C6—C5−178.36 (14)O3—N5—C17—C22−173.11 (13)
C7—N2—C6—C10.86 (14)C22—C17—C18—C190.6 (2)
C4—C5—C6—N2177.88 (13)N5—C17—C18—C19−178.90 (12)
C4—C5—C6—C1−1.2 (2)C17—C18—C19—C20−0.1 (2)
C2—C1—C6—N2−178.38 (12)C17—C18—C19—N6177.32 (12)
N1—C1—C6—N2−0.12 (13)O5—N6—C19—C18162.30 (14)
C2—C1—C6—C50.92 (19)O4—N6—C19—C18−19.0 (2)
N1—C1—C6—C5179.19 (12)O5—N6—C19—C20−20.2 (2)
C1—N1—C7—N21.27 (14)O4—N6—C19—C20158.52 (15)
Co—N1—C7—N2−178.79 (8)C18—C19—C20—O6173.77 (13)
C1—N1—C7—C8−175.73 (12)N6—C19—C20—O6−3.5 (2)
Co—N1—C7—C84.21 (18)C18—C19—C20—C21−2.18 (18)
C6—N2—C7—N1−1.38 (15)N6—C19—C20—C21−179.48 (12)
C6—N2—C7—C8175.65 (12)O6—C20—C21—C22−171.77 (14)
C9—O1—C8—C7−77.34 (13)C19—C20—C21—C224.36 (19)
N1—C7—C8—O1−26.34 (18)O6—C20—C21—N77.1 (2)
N2—C7—C8—O1156.97 (11)C19—C20—C21—N7−176.76 (12)
C8—O1—C9—C10153.52 (10)O7—N7—C21—C22−140.26 (15)
C16—N3—C10—N4−1.25 (14)O8—N7—C21—C2237.34 (19)
Co—N3—C10—N4177.02 (8)O7—N7—C21—C2040.78 (19)
C16—N3—C10—C9179.16 (11)O8—N7—C21—C20−141.62 (13)
Co—N3—C10—C9−2.57 (16)C20—C21—C22—C17−4.2 (2)
C11—N4—C10—N30.67 (15)N7—C21—C22—C17176.93 (12)
C11—N4—C10—C9−179.76 (12)C18—C17—C22—C211.5 (2)
O1—C9—C10—N3−38.59 (16)N5—C17—C22—C21−179.07 (12)

Symmetry codes: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2N···O6ii0.86 (1)1.89 (1)2.6746 (14)151 (2)
N2—H2N···O5ii0.86 (1)2.38 (2)3.0166 (15)131 (2)
N4—H4N···N80.86 (1)2.05 (1)2.9040 (18)172 (2)

Symmetry codes: (ii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2846).

References

  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2004). RAPID-AUTO Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wu, H., Yun, R., Li, K., Tao, S. & Wang, K. (2009). Acta Cryst. E65, m786. [PMC free article] [PubMed]
  • Wu, H., Yun, R., Li, K., Wang, K. & Huang, X. (2009). Acta Cryst. E65, m751–m752. [PMC free article] [PubMed]

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