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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m79.
Published online 2008 December 17. doi:  10.1107/S1600536808041974
PMCID: PMC2967915

Bis(2,2′-bipyridine-κ2 N,N′)(3,5-dinitro-2-oxidobenzoato-κ2 O 1,O 2)cobalt(II)

Abstract

In the title compound, [Co(C7H2N2O7)(C10H8N2)2], the CoII atom is coordinated by four N atoms from two 2,2′-bipyridine ligands and two O atoms from a 3,5-dinitro-2-oxidobenzoate ligand, displaying a distorted octa­hedral coordination geometry. The crystal structure involves C—H(...)O hydrogen bonds between the 2,2′-bipyridine ligands and the carboxyl­ate and NO2 groups of the 3,5-dinitro-2-oxidobenzoate ligand.

Related literature

For general background, see: Lemoine et al. (2004 [triangle]); Wen et al. (2007a [triangle],b [triangle]); Wen & Xie (2007 [triangle]); Yin et al. (2004 [triangle]). For related structures, see: Wen et al. (2007c [triangle],d [triangle]); Wen & Liu (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-00m79-scheme1.jpg

Experimental

Crystal data

  • [Co(C7H2N2O7)(C10H8N2)2]
  • M r = 597.40
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00m79-efi1.jpg
  • a = 8.103 (3) Å
  • b = 21.767 (7) Å
  • c = 14.335 (4) Å
  • β = 95.804 (13)°
  • V = 2515.4 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.74 mm−1
  • T = 293 (2) K
  • 0.22 × 0.20 × 0.18 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: none
  • 19627 measured reflections
  • 4427 independent reflections
  • 2952 reflections with I > 2σ(I)
  • R int = 0.080

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.090
  • S = 1.02
  • 4427 reflections
  • 370 parameters
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 [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 I, global. DOI: 10.1107/S1600536808041974/hy2168sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041974/hy2168Isup2.hkl

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

Acknowledgments

This work was supported financially by the Education Department of Fujian Province (grant No. JA02261) and Longyan Science & Technology Bureau (grant No. 2003LY03).

supplementary crystallographic information

Comment

Much attention has been paid to metal–salicylate complexes owing to their intriguing structural features and biological applications (Lemoine et al., 2004; Wen et al., 2007a, b; Wen & Xie, 2007; Yin et al., 2004). The assembly process of coordination complexes is highly influenced by lots of factors, such as the structural characteristic of organic ligands, the coordination nature of metal ions, pH value of solution, the metal-to-ligand ratio, counter ions and so on. For example, it has been reported that hydrothermal reactions of Co(CH3COO)2.4H2O, 3,5-dinitro-2-oxidobenzoic acid (3,5-dnsalH2) and 2,2'-bipyridine (2,2'-bipy) at different reaction duration give two neutral isomeric metallomacrocycles, Co4(2,2'-bipy)4(3,5-dnsal)4 (Wen et al., 2007c). We report here the structure of a new CoII complex with 3,5-dnsal ligand (Wen & Liu, 2007; Wen et al., 2007d).

The title complex was synthesized under hydrothermal conditions. The CoII atom is coordinated in a distorted octahedral coordination geometry by two O atoms from a 3,5-dnsal ligand and four N atoms from two 2,2'-bipy ligands (Fig.1 and Table 1). The carboxylate group of the 3,5-dnsal ligand is rotated relatively to the aromatic ring with a dihedral angle of 36.8 (2)°. The two pyridyl rings of the 2,2'-bipy ligand containing N5 and N6 are approximately coplanar, exhibiting a dihedral angle of 2.2 (2)°, while the two pyridyl rings of the other 2,2'-bipy containing N3 and N4 deviate from coplanarity with a dihedral angle of 10.6 (2)°. The adjacent mononuclear complex molecules are further connected to each other by C—H···O hydrogen bonds formed between the 2,2'-bipy ligands and the carboxylate and NO2 groups of the 3,5-dnsal ligand, resulting in a three-dimensional network structure (Table 2 and Fig. 2).

Experimental

A mixture of Co(NO3)2.4H2O (0.1 mmol), 2,2'-bipyridine (0.2 mmol), 2-hydroxy-3,5-dinitrobenzoic acid (0.2 mmol) and distilled water (10 ml) was put into a 20 ml Teflon-lined autoclave and then heated at 423 K for 72 h. Brown block-like crystals of the title compound suitable for X-ray analysis were collected from the reaction mixture.

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
Molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity.
Fig. 2.
A packing view of the title compound. Hydrogen bonds are represented by dashed lines.

Crystal data

[Co(C7H2N2O7)(C10H8N2)2]F(000) = 1220
Mr = 597.40Dx = 1.578 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4427 reflections
a = 8.103 (3) Åθ = 3.0–25.0°
b = 21.767 (7) ŵ = 0.74 mm1
c = 14.335 (4) ÅT = 293 K
β = 95.804 (13)°Block, brown
V = 2515.4 (15) Å30.22 × 0.20 × 0.18 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer2952 reflections with I > 2σ(I)
Radiation source: 18 kW rotating anodeRint = 0.080
graphiteθmax = 25.0°, θmin = 3.0°
ω scansh = −9→9
19627 measured reflectionsk = −25→25
4427 independent reflectionsl = −17→15

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) = 0.090H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0295P)2 + 0.2101P] where P = (Fo2 + 2Fc2)/3
4427 reflections(Δ/σ)max = 0.001
370 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = −0.31 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Co10.63835 (5)0.37028 (2)0.82451 (3)0.03493 (13)
N10.4828 (4)0.32130 (14)0.51277 (18)0.0486 (7)
N20.7733 (4)0.49718 (17)0.4014 (2)0.0556 (8)
N30.5787 (3)0.27604 (12)0.84364 (17)0.0406 (6)
N40.8319 (3)0.32190 (13)0.76558 (16)0.0402 (7)
N50.4405 (3)0.40721 (12)0.89234 (16)0.0380 (6)
N60.7350 (3)0.37120 (13)0.96914 (16)0.0406 (6)
O10.6901 (4)0.54777 (12)0.73884 (16)0.0853 (10)
O20.7262 (3)0.45655 (10)0.80574 (13)0.0448 (6)
O30.5155 (3)0.37447 (11)0.69267 (13)0.0433 (5)
O40.3629 (3)0.30618 (14)0.55073 (18)0.0773 (9)
O50.5399 (3)0.28916 (14)0.4535 (2)0.0791 (9)
O60.7632 (4)0.47298 (14)0.32404 (17)0.0844 (9)
O70.8431 (4)0.54639 (15)0.41780 (19)0.0820 (9)
C10.6593 (4)0.46131 (15)0.63950 (19)0.0380 (8)
C20.5739 (3)0.40396 (15)0.62656 (19)0.0346 (7)
C30.5590 (3)0.38110 (15)0.53228 (19)0.0366 (8)
C40.6228 (4)0.41067 (17)0.4597 (2)0.0431 (8)
H4A0.61220.39370.39980.052*
C50.7027 (4)0.46570 (16)0.4764 (2)0.0414 (8)
C60.7186 (4)0.49101 (16)0.5656 (2)0.0439 (8)
H6A0.77050.52890.57550.053*
C70.6922 (5)0.49138 (17)0.7350 (2)0.0487 (9)
C80.4572 (4)0.25584 (18)0.8922 (2)0.0540 (9)
H8A0.38150.28430.91100.065*
C90.4385 (5)0.19578 (19)0.9155 (3)0.0603 (10)
H9A0.35360.18360.95050.072*
C100.5475 (5)0.15383 (18)0.8863 (3)0.0616 (11)
H10A0.53730.11250.90110.074*
C110.6722 (4)0.17293 (17)0.8349 (2)0.0527 (9)
H11A0.74620.14470.81380.063*
C120.6856 (4)0.23450 (15)0.8153 (2)0.0393 (8)
C130.8198 (4)0.26042 (16)0.7643 (2)0.0390 (8)
C140.9282 (5)0.2248 (2)0.7189 (3)0.0665 (11)
H14A0.91840.18220.71820.080*
C151.0509 (6)0.2531 (2)0.6748 (3)0.0821 (14)
H15A1.12460.22980.64380.098*
C161.0640 (5)0.3156 (2)0.6767 (3)0.0697 (12)
H16A1.14740.33540.64830.084*
C170.9511 (4)0.34852 (18)0.7214 (2)0.0502 (9)
H17A0.95760.39120.72110.060*
C180.2951 (4)0.42475 (16)0.8493 (2)0.0488 (9)
H18A0.27560.41950.78480.059*
C190.1727 (4)0.45027 (18)0.8965 (3)0.0586 (10)
H19A0.07190.46200.86470.070*
C200.2032 (5)0.45792 (19)0.9916 (3)0.0638 (11)
H20A0.12230.47501.02520.077*
C210.3512 (4)0.44060 (17)1.0369 (2)0.0521 (9)
H21A0.37240.44571.10150.063*
C220.4693 (4)0.41536 (14)0.98594 (19)0.0379 (8)
C230.6354 (4)0.39596 (15)1.02814 (19)0.0404 (8)
C240.6875 (5)0.40303 (18)1.1225 (2)0.0591 (10)
H24A0.61750.42071.16260.071*
C250.8424 (6)0.3838 (2)1.1559 (3)0.0773 (14)
H25A0.87980.38901.21900.093*
C260.9425 (5)0.3570 (2)1.0962 (3)0.0695 (12)
H26A1.04730.34261.11810.083*
C270.8848 (4)0.35174 (17)1.0030 (2)0.0538 (10)
H27A0.95300.33390.96210.065*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.0425 (2)0.0350 (3)0.0287 (2)0.0003 (2)0.01106 (17)−0.0013 (2)
N10.0501 (17)0.058 (2)0.0394 (15)−0.0070 (15)0.0118 (14)−0.0117 (15)
N20.074 (2)0.058 (2)0.0390 (17)0.0131 (18)0.0248 (16)0.0142 (16)
N30.0478 (16)0.0348 (17)0.0400 (14)−0.0024 (13)0.0090 (13)−0.0019 (13)
N40.0391 (15)0.0479 (19)0.0350 (13)0.0013 (13)0.0109 (12)−0.0020 (13)
N50.0447 (15)0.0381 (17)0.0330 (13)0.0002 (12)0.0134 (12)−0.0013 (12)
N60.0463 (16)0.0409 (17)0.0352 (13)−0.0016 (14)0.0068 (12)0.0006 (13)
O10.181 (3)0.0328 (17)0.0465 (14)−0.0150 (18)0.0308 (17)−0.0052 (12)
O20.0609 (14)0.0401 (14)0.0334 (11)−0.0088 (12)0.0056 (11)−0.0045 (10)
O30.0481 (12)0.0498 (15)0.0329 (11)−0.0093 (12)0.0087 (10)0.0011 (11)
O40.0691 (17)0.096 (3)0.0724 (17)−0.0359 (16)0.0336 (15)−0.0251 (16)
O50.084 (2)0.073 (2)0.0871 (19)−0.0207 (16)0.0400 (17)−0.0407 (17)
O60.134 (3)0.087 (2)0.0378 (13)−0.0046 (19)0.0406 (16)0.0051 (15)
O70.120 (3)0.065 (2)0.0671 (17)−0.0198 (19)0.0384 (17)0.0127 (16)
C10.0483 (19)0.036 (2)0.0308 (15)0.0044 (16)0.0119 (14)0.0000 (14)
C20.0349 (17)0.039 (2)0.0307 (15)0.0061 (15)0.0075 (14)0.0022 (14)
C30.0349 (16)0.044 (2)0.0322 (15)0.0040 (15)0.0074 (13)−0.0035 (15)
C40.0462 (19)0.056 (2)0.0289 (15)0.0142 (17)0.0099 (15)0.0000 (16)
C50.050 (2)0.045 (2)0.0314 (16)0.0123 (17)0.0154 (15)0.0075 (15)
C60.057 (2)0.036 (2)0.0407 (18)0.0039 (16)0.0148 (16)0.0030 (15)
C70.075 (2)0.036 (2)0.0376 (18)−0.0123 (19)0.0200 (18)−0.0043 (17)
C80.052 (2)0.050 (3)0.064 (2)−0.0062 (18)0.0217 (19)0.0009 (19)
C90.057 (2)0.054 (3)0.072 (2)−0.016 (2)0.017 (2)0.005 (2)
C100.064 (3)0.040 (2)0.078 (3)−0.011 (2)−0.001 (2)0.012 (2)
C110.052 (2)0.037 (2)0.067 (2)0.0040 (17)−0.0032 (19)−0.0035 (19)
C120.0463 (19)0.036 (2)0.0348 (16)0.0023 (16)−0.0007 (15)−0.0042 (15)
C130.0413 (18)0.042 (2)0.0342 (16)0.0051 (16)0.0073 (15)−0.0038 (16)
C140.082 (3)0.051 (3)0.072 (2)0.012 (2)0.033 (2)−0.009 (2)
C150.093 (3)0.071 (3)0.092 (3)0.018 (3)0.057 (3)−0.008 (3)
C160.066 (3)0.073 (3)0.077 (3)0.002 (2)0.044 (2)−0.001 (2)
C170.052 (2)0.051 (2)0.0510 (19)−0.0008 (17)0.0215 (18)0.0010 (17)
C180.049 (2)0.053 (2)0.0446 (18)0.0058 (18)0.0074 (17)−0.0025 (17)
C190.046 (2)0.060 (3)0.071 (2)0.0125 (19)0.0112 (19)−0.006 (2)
C200.062 (3)0.060 (3)0.074 (3)0.008 (2)0.033 (2)−0.015 (2)
C210.064 (2)0.051 (3)0.0445 (18)0.0018 (19)0.0237 (18)−0.0062 (17)
C220.052 (2)0.0319 (19)0.0329 (15)−0.0045 (15)0.0177 (15)−0.0032 (14)
C230.060 (2)0.0330 (19)0.0294 (15)−0.0070 (16)0.0102 (16)0.0016 (14)
C240.084 (3)0.060 (3)0.0338 (17)−0.003 (2)0.0084 (19)−0.0005 (18)
C250.102 (3)0.087 (4)0.039 (2)0.001 (3)−0.011 (2)0.005 (2)
C260.071 (3)0.077 (3)0.056 (2)0.009 (2)−0.012 (2)0.013 (2)
C270.051 (2)0.062 (3)0.0471 (19)0.0014 (18)0.0008 (17)0.0042 (18)

Geometric parameters (Å, °)

Co1—O22.036 (2)C8—H8A0.9300
Co1—O32.047 (2)C9—C101.365 (5)
Co1—N52.116 (2)C9—H9A0.9300
Co1—N32.132 (3)C10—C111.373 (5)
Co1—N42.133 (3)C10—H10A0.9300
Co1—N62.141 (2)C11—C121.376 (5)
N1—O41.206 (3)C11—H11A0.9300
N1—O51.227 (3)C12—C131.482 (4)
N1—C31.456 (4)C13—C141.382 (5)
N2—O61.223 (4)C14—C151.377 (6)
N2—O71.223 (4)C14—H14A0.9300
N2—C51.441 (4)C15—C161.365 (6)
N3—C81.336 (4)C15—H15A0.9300
N3—C121.343 (4)C16—C171.370 (5)
N4—C171.339 (4)C16—H16A0.9300
N4—C131.342 (4)C17—H17A0.9300
N5—C181.329 (4)C18—C191.373 (5)
N5—C221.350 (3)C18—H18A0.9300
N6—C271.330 (4)C19—C201.371 (5)
N6—C231.340 (4)C19—H19A0.9300
O1—C71.229 (4)C20—C211.359 (5)
O2—C71.274 (4)C20—H20A0.9300
O3—C21.275 (3)C21—C221.376 (4)
C1—C61.369 (4)C21—H21A0.9300
C1—C21.430 (4)C22—C231.480 (4)
C1—C71.516 (4)C23—C241.384 (4)
C2—C31.434 (4)C24—C251.364 (5)
C3—C41.369 (4)C24—H24A0.9300
C4—C51.371 (5)C25—C261.369 (6)
C4—H4A0.9300C25—H25A0.9300
C5—C61.387 (4)C26—C271.375 (5)
C6—H6A0.9300C26—H26A0.9300
C8—C91.362 (5)C27—H27A0.9300
O2—Co1—O388.90 (8)C9—C8—H8A118.3
O2—Co1—N590.10 (10)C8—C9—C10118.4 (4)
O3—Co1—N595.00 (9)C8—C9—H9A120.8
O2—Co1—N3172.56 (10)C10—C9—H9A120.8
O3—Co1—N393.79 (9)C9—C10—C11119.7 (4)
N5—Co1—N396.56 (10)C9—C10—H10A120.1
O2—Co1—N497.01 (10)C11—C10—H10A120.1
O3—Co1—N487.98 (9)C10—C11—C12118.8 (4)
N5—Co1—N4172.36 (11)C10—C11—H11A120.6
N3—Co1—N476.19 (11)C12—C11—H11A120.6
O2—Co1—N691.19 (9)N3—C12—C11121.8 (3)
O3—Co1—N6171.78 (10)N3—C12—C13114.9 (3)
N5—Co1—N676.78 (10)C11—C12—C13123.3 (3)
N3—Co1—N687.14 (10)N4—C13—C14121.1 (3)
N4—Co1—N6100.17 (10)N4—C13—C12115.4 (3)
O4—N1—O5122.3 (3)C14—C13—C12123.5 (3)
O4—N1—C3120.2 (3)C15—C14—C13119.2 (4)
O5—N1—C3117.4 (3)C15—C14—H14A120.4
O6—N2—O7122.6 (3)C13—C14—H14A120.4
O6—N2—C5118.5 (4)C16—C15—C14119.7 (4)
O7—N2—C5118.9 (3)C16—C15—H15A120.2
C8—N3—C12117.9 (3)C14—C15—H15A120.2
C8—N3—Co1124.9 (2)C15—C16—C17118.4 (4)
C12—N3—Co1116.6 (2)C15—C16—H16A120.8
C17—N4—C13118.7 (3)C17—C16—H16A120.8
C17—N4—Co1124.6 (3)N4—C17—C16122.8 (4)
C13—N4—Co1116.2 (2)N4—C17—H17A118.6
C18—N5—C22118.6 (3)C16—C17—H17A118.6
C18—N5—Co1125.0 (2)N5—C18—C19122.6 (3)
C22—N5—Co1116.3 (2)N5—C18—H18A118.7
C27—N6—C23118.9 (3)C19—C18—H18A118.7
C27—N6—Co1125.5 (2)C20—C19—C18118.2 (3)
C23—N6—Co1115.5 (2)C20—C19—H19A120.9
C7—O2—Co1127.1 (2)C18—C19—H19A120.9
C2—O3—Co1121.76 (18)C21—C20—C19120.2 (3)
C6—C1—C2121.0 (3)C21—C20—H20A119.9
C6—C1—C7116.8 (3)C19—C20—H20A119.9
C2—C1—C7122.2 (3)C20—C21—C22119.0 (3)
O3—C2—C1123.7 (3)C20—C21—H21A120.5
O3—C2—C3121.6 (3)C22—C21—H21A120.5
C1—C2—C3114.8 (3)N5—C22—C21121.4 (3)
C4—C3—C2123.5 (3)N5—C22—C23115.3 (3)
C4—C3—N1117.4 (3)C21—C22—C23123.3 (3)
C2—C3—N1119.0 (3)N6—C23—C24121.2 (3)
C3—C4—C5119.0 (3)N6—C23—C22115.9 (2)
C3—C4—H4A120.5C24—C23—C22122.8 (3)
C5—C4—H4A120.5C25—C24—C23119.2 (4)
C4—C5—C6120.4 (3)C25—C24—H24A120.4
C4—C5—N2120.0 (3)C23—C24—H24A120.4
C6—C5—N2119.5 (3)C24—C25—C26119.5 (3)
C1—C6—C5121.3 (3)C24—C25—H25A120.2
C1—C6—H6A119.4C26—C25—H25A120.2
C5—C6—H6A119.4C25—C26—C27118.6 (4)
O1—C7—O2124.2 (3)C25—C26—H26A120.7
O1—C7—C1118.0 (3)C27—C26—H26A120.7
O2—C7—C1117.8 (3)N6—C27—C26122.4 (4)
N3—C8—C9123.4 (4)N6—C27—H27A118.8
N3—C8—H8A118.3C26—C27—H27A118.8
O3—Co1—N3—C8−100.0 (3)C2—C1—C6—C5−2.1 (5)
N5—Co1—N3—C8−4.6 (3)C7—C1—C6—C5176.5 (3)
N4—Co1—N3—C8173.0 (3)C4—C5—C6—C11.7 (5)
N6—Co1—N3—C871.8 (3)N2—C5—C6—C1−177.3 (3)
O3—Co1—N3—C1289.3 (2)Co1—O2—C7—O1149.7 (3)
N5—Co1—N3—C12−175.2 (2)Co1—O2—C7—C1−32.9 (4)
N4—Co1—N3—C122.4 (2)C6—C1—C7—O135.5 (5)
N6—Co1—N3—C12−98.9 (2)C2—C1—C7—O1−145.9 (4)
O2—Co1—N4—C17−7.7 (2)C6—C1—C7—O2−142.0 (3)
O3—Co1—N4—C1781.0 (2)C2—C1—C7—O236.6 (5)
N3—Co1—N4—C17175.4 (3)C12—N3—C8—C91.2 (5)
N6—Co1—N4—C17−100.2 (2)Co1—N3—C8—C9−169.4 (3)
O2—Co1—N4—C13−179.9 (2)N3—C8—C9—C10−1.3 (6)
O3—Co1—N4—C13−91.2 (2)C8—C9—C10—C110.2 (5)
N3—Co1—N4—C133.2 (2)C9—C10—C11—C121.0 (5)
N6—Co1—N4—C1387.7 (2)C8—N3—C12—C110.1 (4)
O2—Co1—N5—C1888.5 (3)Co1—N3—C12—C11171.4 (2)
O3—Co1—N5—C18−0.4 (3)C8—N3—C12—C13−178.3 (3)
N3—Co1—N5—C18−94.8 (3)Co1—N3—C12—C13−7.0 (3)
N6—Co1—N5—C18179.7 (3)C10—C11—C12—N3−1.1 (5)
O2—Co1—N5—C22−88.8 (2)C10—C11—C12—C13177.1 (3)
O3—Co1—N5—C22−177.7 (2)C17—N4—C13—C140.4 (4)
N3—Co1—N5—C2287.9 (2)Co1—N4—C13—C14173.0 (2)
N6—Co1—N5—C222.4 (2)C17—N4—C13—C12179.6 (3)
O2—Co1—N6—C27−90.8 (3)Co1—N4—C13—C12−7.8 (3)
N5—Co1—N6—C27179.4 (3)N3—C12—C13—N49.8 (4)
N3—Co1—N6—C2781.9 (3)C11—C12—C13—N4−168.6 (3)
N4—Co1—N6—C276.5 (3)N3—C12—C13—C14−171.1 (3)
O2—Co1—N6—C2386.5 (2)C11—C12—C13—C1410.5 (5)
N5—Co1—N6—C23−3.3 (2)N4—C13—C14—C150.3 (5)
N3—Co1—N6—C23−100.8 (2)C12—C13—C14—C15−178.8 (3)
N4—Co1—N6—C23−176.2 (2)C13—C14—C15—C160.2 (6)
O3—Co1—O2—C73.1 (3)C14—C15—C16—C17−1.2 (7)
N5—Co1—O2—C7−91.9 (3)C13—N4—C17—C16−1.6 (5)
N4—Co1—O2—C791.0 (3)Co1—N4—C17—C16−173.6 (3)
N6—Co1—O2—C7−168.6 (3)C15—C16—C17—N42.0 (6)
O2—Co1—O3—C232.9 (2)C22—N5—C18—C19−0.6 (5)
N5—Co1—O3—C2122.9 (2)Co1—N5—C18—C19−177.9 (3)
N3—Co1—O3—C2−140.2 (2)N5—C18—C19—C200.2 (6)
N4—Co1—O3—C2−64.2 (3)C18—C19—C20—C210.1 (6)
Co1—O3—C2—C1−38.2 (4)C19—C20—C21—C220.0 (6)
Co1—O3—C2—C3141.4 (2)C18—N5—C22—C210.7 (5)
C6—C1—C2—O3−179.7 (3)Co1—N5—C22—C21178.2 (3)
C7—C1—C2—O31.8 (5)C18—N5—C22—C23−178.7 (3)
C6—C1—C2—C30.7 (4)Co1—N5—C22—C23−1.2 (4)
C7—C1—C2—C3−177.8 (3)C20—C21—C22—N5−0.4 (5)
O3—C2—C3—C4−178.6 (3)C20—C21—C22—C23178.9 (3)
C1—C2—C3—C41.0 (4)C27—N6—C23—C241.8 (5)
O3—C2—C3—N1−3.2 (4)Co1—N6—C23—C24−175.7 (3)
C1—C2—C3—N1176.4 (3)C27—N6—C23—C22−178.7 (3)
O4—N1—C3—C4−144.3 (3)Co1—N6—C23—C223.8 (4)
O5—N1—C3—C432.0 (4)N5—C22—C23—N6−1.8 (4)
O4—N1—C3—C239.9 (4)C21—C22—C23—N6178.8 (3)
O5—N1—C3—C2−143.7 (3)N5—C22—C23—C24177.7 (3)
C2—C3—C4—C5−1.3 (5)C21—C22—C23—C24−1.7 (5)
N1—C3—C4—C5−176.9 (3)N6—C23—C24—C25−0.7 (6)
C3—C4—C5—C60.0 (5)C22—C23—C24—C25179.9 (4)
C3—C4—C5—N2179.0 (3)C23—C24—C25—C26−1.2 (6)
O6—N2—C5—C4−1.7 (5)C24—C25—C26—C271.8 (7)
O7—N2—C5—C4179.5 (3)C23—N6—C27—C26−1.1 (5)
O6—N2—C5—C6177.4 (3)Co1—N6—C27—C26176.1 (3)
O7—N2—C5—C6−1.4 (5)C25—C26—C27—N6−0.7 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C11—H11A···O1i0.932.323.166 (5)151
C21—H21A···O1ii0.932.403.275 (4)157
C16—H16A···O4iii0.932.433.171 (5)137
C25—H25A···O6iv0.932.613.209 (5)123
C9—H9A···O5v0.932.613.346 (5)136

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2168).

References

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