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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1415–m1416.
Published online 2010 October 20. doi:  10.1107/S1600536810040602
PMCID: PMC3009208

Aqua­(hippurato)bis­(1,10-phenanthroline)cobalt(II) nitrate monohydrate

Abstract

In the title compound, [Co(C9H8NO3)(C12H8N2)2(H2O)]NO3·H2O, the CoII atom is six-coordinated by a carboxylate O atom of the hippurate (Hc) anion, a water O atom and four N atoms from two 1,10-phenanthroline ligands in a distorted octa­hedral geometry. The uncoordinated O atom of the hippuric acid anion is involved in an intra­molecular hydrogen bond to the coordinated water mol­ecule. The crystal packing is stabilized by inter­molecular O—H(...)O hydrogen bonds involving the Hc anions, the coordinated water mol­ecule, the nitrate anion and the uncoordinated water mol­ecule.

Related literature

For complexes based on hippuric acid, see: Antolini et al. (1982 [triangle]); Brown & Trefonas (1973 [triangle]); Grewe et al. (1982 [triangle]); Guo, Chen et al. (2006 [triangle]); Guo, Wang et al. (2006 [triangle]); Morelock et al. (1979 [triangle], 1982 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1415-scheme1.jpg

Experimental

Crystal data

  • [Co(C9H8NO3)(C12H8N2)2(H2O)]NO3·H2O
  • M r = 695.54
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1415-efi1.jpg
  • a = 9.935 (2) Å
  • b = 13.991 (3) Å
  • c = 23.162 (5) Å
  • β = 91.37 (3)°
  • V = 3218.7 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.60 mm−1
  • T = 291 K
  • 0.20 × 0.18 × 0.17 mm

Data collection

  • Bruker P4 diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.890, T max = 0.906
  • 9187 measured reflections
  • 5493 independent reflections
  • 3848 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.143
  • S = 1.09
  • 5493 reflections
  • 445 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810040602/kp2275sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040602/kp2275Isup2.hkl

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

Acknowledgments

The authors thank the Youth Foundation of Jiangxi Provincial Office of Education (GJJ09605) and the Science Foundation of Jiangxi Provincial Office of Education (GJJ09637).

supplementary crystallographic information

Comment

Hippuric acid (Hc) is a naturally occurring carboxylic acid found in the urine of most mammals. Several decades ago, hippuric acid was testified as a good building units for metal complexes with desirable magnetic properties, due to the carboxylic group of hippuric acid can act as donor to link metal centers. To date, the synthesis, crystal structures, and related property studying of Ni(II), Fe(II), Zn(II), Cu(II) complexes based on hippuric acid have been reported (Antolini, et al., 1982; Brown, et al., 1973; Grewe, et al., 1982; Guo, Wang, Chen, et al., 2006; Guo, Chen, Wang, et al., 2006; Morelock, Good, Trefonas, Karraker et al., 1979; Morelock, Good, Trefonas, Majeste et al., 1982). Herein, we present the synthesis and crystal structure of its Co(II) complex.

The title compound, (I), is a mononuclear complex, consisting of one [Co(Hc)(phen)2(H2O)]+ unit, one NO3- anion, and one crystal H2O molecule (Fig. 1). The Co(II) ion is six-coordinated by O atoms from one Hc anion and one water molecule, four N atoms of two 1,10-phen ligands in a shape of distorted octahedron. The atoms N2, N3, N5, and O4 are located in the equatorial plane whereas O2 and N4 occupy the axial positions. The bond distances and angles around Co atom reveal a distorted octahedron (bite-chelating angles are 77.2 and 77.822 °). The Hc anion acts as a monodentate ligand, with one of the carboylic oxygen atoms coordinated to the Co(II) ions, while the amide O and imine N atoms remain uncoordinated.

The coordinated water molecule and the crystal water molecule donate H atom to the nitrate anion and to the Hc anion ligand to form O—H···O hydrogen bonds. In addition, the imine group of the Hc anion also donate H atom to the nitrate to form N—H···O hydrogen bonds (Table 1, Fig. 2).

Experimental

Hippuric acid (1.0 mmol) , Co(NO3)2.6H2 (O1.0 mmol) and 1,10-phenanthroline (2.0 mmol) were dissolved in a water-ethanol mixture(v/v=1:4; 25 ml). The obtained solution was continously stirred, and its pH was adjusted to 6–7 by 1.0 mol L-1 NaOH aqueous solution. Then the mixture was further stirred for ca 2 h at room temperature and filtered. The resultant filtrate was left to stand for slow evaporation at room temperature. Dark-red single crystals of (I) suitable for X-ray diffraction analysis were obtained after two weeks (yield 66%).

Refinement

Hydrogen atoms attached to carbon atoms and nitrogen atoms were positioned geometrically and treated as riding, with C—H = 0.93 Å, N—H = 0.86 Å, and Uiso(H) = 1.2Ueq(C or N). The hydrogen atoms of the coordination water molecules and lattice water molecules were assigned in the difference Fourier maps and refined isotropically.

Figures

Fig. 1.
The molecular structure of (I) (hydrogen bonds are shown by dashed lines).
Fig. 2.
The crystal packing of (I) stabilised by intermolecular hydrogen bonds (dashed lines).

Crystal data

[Co(C9H8NO3)(C12H8N2)2(H2O)]NO3·H2OF(000) = 1436
Mr = 695.54Dx = 1.435 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1226 reflections
a = 9.935 (2) Åθ = 1.7–25.5°
b = 13.991 (3) ŵ = 0.60 mm1
c = 23.162 (5) ÅT = 291 K
β = 91.37 (3)°Prismatic, dark-red
V = 3218.7 (11) Å30.20 × 0.18 × 0.17 mm
Z = 4

Data collection

Bruker P4 diffractometer5493 independent reflections
Radiation source: fine-focus sealed tube3848 reflections with I > 2σ(I)
graphiteRint = 0.043
ω scansθmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = 0→12
Tmin = 0.890, Tmax = 0.906k = −16→16
9187 measured reflectionsl = −28→28

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.143w = 1/[σ2(Fo2) + (0.0588P)2 + 1.9834P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
5493 reflectionsΔρmax = 0.53 e Å3
445 parametersΔρmin = −0.30 e Å3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0026 (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*/Ueq
Co10.22952 (5)0.25150 (4)0.93865 (2)0.03887 (18)
N10.2492 (4)0.0562 (3)0.77418 (15)0.0519 (10)
N20.0799 (4)0.1728 (2)0.98300 (14)0.0457 (9)
N30.0537 (3)0.2743 (2)0.88506 (14)0.0427 (8)
N40.1985 (4)0.3762 (2)0.99264 (15)0.0474 (9)
N50.3523 (3)0.3570 (2)0.89962 (15)0.0461 (9)
N60.4811 (5)0.2629 (3)0.2140 (2)0.0739 (12)
O10.0673 (4)−0.0126 (3)0.81183 (15)0.0887 (12)
O20.2726 (3)0.15136 (19)0.87560 (12)0.0500 (7)
O30.4124 (3)0.0438 (2)0.91520 (12)0.0532 (8)
O40.3952 (4)0.1959 (3)0.98609 (17)0.0594 (9)
O50.5553 (6)0.1969 (3)0.2076 (2)0.135 (2)
O60.4928 (5)0.3168 (3)0.25517 (19)0.1063 (15)
O70.3906 (5)0.2794 (3)0.1776 (2)0.1195 (16)
C1−0.1062 (7)0.0710 (5)0.7295 (3)0.098 (2)
H1A−0.13830.02000.75100.118*
C2−0.1936 (10)0.1199 (8)0.6925 (4)0.143 (4)
H2A−0.28330.10150.68900.171*
C3−0.1478 (13)0.1941 (9)0.6619 (4)0.162 (6)
H3A−0.20680.22710.63740.194*
C4−0.0191 (11)0.2214 (6)0.6660 (3)0.128 (3)
H4A0.01000.27290.64420.153*
C50.0727 (7)0.1734 (5)0.7027 (2)0.0872 (18)
H5A0.16220.19270.70530.105*
C60.0286 (5)0.0969 (4)0.7350 (2)0.0635 (13)
C70.1167 (6)0.0431 (3)0.77715 (19)0.0585 (13)
C80.3383 (5)0.0180 (3)0.81921 (18)0.0573 (12)
H8A0.42890.01490.80460.069*
H8B0.3103−0.04670.82800.069*
C90.3408 (4)0.0765 (3)0.87478 (17)0.0416 (10)
C100.0916 (6)0.1286 (3)1.0340 (2)0.0655 (14)
H10A0.17440.12861.05360.079*
C11−0.0189 (8)0.0818 (4)1.0587 (2)0.0839 (19)
H11A−0.00940.05341.09490.101*
C12−0.1382 (7)0.0784 (4)1.0298 (3)0.0837 (19)
H12A−0.21120.04731.04580.100*
C13−0.1515 (5)0.1217 (3)0.9762 (3)0.0679 (15)
C14−0.0405 (4)0.1707 (3)0.9552 (2)0.0483 (11)
C20−0.2734 (6)0.1177 (4)0.9418 (4)0.095 (2)
H20A−0.34720.08460.95550.114*
C15−0.0536 (4)0.2210 (3)0.90145 (19)0.0462 (11)
C16−0.1735 (5)0.2160 (3)0.8682 (3)0.0664 (14)
C17−0.1808 (7)0.2669 (4)0.8170 (2)0.0786 (18)
H17A−0.25830.26420.79370.094*
C18−0.0740 (7)0.3207 (4)0.8007 (2)0.0808 (18)
H18A−0.07850.35620.76670.097*
C190.0429 (5)0.3219 (3)0.83589 (19)0.0609 (13)
H19A0.11610.35790.82410.073*
C21−0.2826 (6)0.1609 (4)0.8902 (4)0.090 (2)
H21A−0.36160.15510.86820.108*
C220.1209 (5)0.3858 (3)1.0377 (2)0.0638 (13)
H22A0.06960.33371.04880.077*
C230.1115 (6)0.4693 (4)1.0694 (2)0.0798 (17)
H23A0.05500.47281.10070.096*
C240.1866 (6)0.5465 (4)1.0538 (2)0.0757 (16)
H24A0.18210.60281.07500.091*
C250.2702 (5)0.5411 (3)1.0064 (2)0.0570 (12)
C260.2721 (4)0.4529 (3)0.97703 (18)0.0449 (10)
C270.3558 (4)0.4429 (3)0.92735 (18)0.0431 (10)
C280.4375 (5)0.5187 (3)0.9108 (2)0.0538 (12)
C290.5179 (5)0.5031 (4)0.8623 (2)0.0714 (15)
H29A0.57380.55150.84940.086*
C300.5141 (5)0.4184 (4)0.8347 (2)0.0706 (15)
H30A0.56770.40790.80290.085*
C310.4292 (5)0.3463 (3)0.8541 (2)0.0601 (13)
H31A0.42650.28850.83430.072*
C320.3542 (6)0.6170 (3)0.9870 (3)0.0743 (16)
H32A0.35320.67521.00640.089*
C330.4342 (6)0.6065 (3)0.9417 (3)0.0735 (16)
H33A0.48820.65720.93040.088*
O80.4361 (6)0.1252 (3)0.09134 (17)0.133 (2)
H8F0.48280.07450.08930.200*
H8E0.41210.14590.12490.200*
H1G0.289 (8)0.100 (5)0.754 (3)0.160*
H4F0.394 (7)0.141 (5)0.970 (3)0.14 (3)*
H4E0.395 (6)0.178 (4)1.022 (3)0.09 (2)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.0449 (3)0.0334 (3)0.0384 (3)−0.0027 (3)0.0039 (2)−0.0031 (3)
N10.069 (3)0.046 (2)0.041 (2)0.0013 (19)0.0017 (19)−0.0084 (17)
N20.055 (2)0.0399 (18)0.042 (2)−0.0044 (16)0.0069 (17)0.0000 (16)
N30.051 (2)0.0357 (18)0.0412 (19)0.0074 (15)0.0003 (16)−0.0021 (15)
N40.055 (2)0.0408 (19)0.046 (2)0.0010 (17)0.0041 (17)−0.0075 (16)
N50.047 (2)0.0363 (18)0.055 (2)−0.0043 (16)0.0056 (18)0.0003 (16)
N60.085 (4)0.064 (3)0.073 (3)0.003 (3)0.010 (3)0.001 (3)
O10.107 (3)0.094 (3)0.065 (2)−0.038 (2)0.010 (2)0.014 (2)
O20.063 (2)0.0417 (16)0.0450 (16)0.0120 (15)−0.0001 (14)−0.0061 (13)
O30.056 (2)0.0510 (17)0.0520 (18)0.0099 (15)−0.0090 (15)−0.0051 (15)
O40.067 (2)0.057 (2)0.053 (2)0.0065 (17)−0.0120 (17)−0.0105 (18)
O50.145 (5)0.098 (3)0.162 (5)0.057 (3)−0.007 (4)−0.042 (3)
O60.154 (4)0.086 (3)0.080 (3)0.009 (3)0.029 (3)−0.020 (3)
O70.113 (4)0.108 (4)0.137 (4)−0.013 (3)−0.025 (3)0.016 (3)
C10.089 (5)0.108 (5)0.097 (5)0.002 (4)−0.011 (4)−0.047 (4)
C20.090 (6)0.198 (11)0.138 (9)0.035 (7)−0.051 (7)−0.090 (7)
C30.163 (12)0.230 (13)0.091 (7)0.116 (11)−0.047 (7)−0.060 (7)
C40.167 (8)0.162 (8)0.054 (4)0.085 (7)0.013 (5)0.024 (4)
C50.104 (5)0.107 (5)0.051 (3)0.029 (4)0.012 (3)0.014 (3)
C60.065 (4)0.079 (3)0.047 (3)0.005 (3)−0.002 (2)−0.024 (3)
C70.086 (4)0.051 (3)0.038 (2)−0.011 (3)0.003 (3)−0.011 (2)
C80.076 (3)0.048 (3)0.048 (3)0.010 (2)−0.006 (2)−0.007 (2)
C90.045 (3)0.035 (2)0.044 (2)−0.0057 (19)0.003 (2)0.0005 (19)
C100.097 (4)0.056 (3)0.044 (3)−0.005 (3)0.011 (3)0.005 (2)
C110.140 (6)0.052 (3)0.061 (3)−0.009 (4)0.044 (4)0.008 (3)
C120.091 (5)0.060 (3)0.103 (5)−0.017 (3)0.055 (4)−0.005 (3)
C130.060 (4)0.049 (3)0.097 (4)−0.007 (2)0.028 (3)−0.011 (3)
C140.046 (3)0.035 (2)0.064 (3)−0.0046 (19)0.011 (2)−0.010 (2)
C200.054 (4)0.064 (4)0.168 (7)−0.014 (3)0.031 (4)−0.014 (4)
C150.043 (3)0.037 (2)0.059 (3)0.0030 (18)−0.002 (2)−0.0172 (19)
C160.053 (3)0.053 (3)0.092 (4)0.011 (2)−0.016 (3)−0.027 (3)
C170.084 (4)0.073 (4)0.077 (4)0.031 (3)−0.035 (3)−0.032 (3)
C180.119 (5)0.071 (4)0.052 (3)0.033 (4)−0.018 (3)−0.005 (3)
C190.080 (4)0.055 (3)0.047 (3)0.011 (3)−0.004 (3)0.003 (2)
C210.043 (3)0.071 (4)0.155 (7)−0.005 (3)−0.009 (4)−0.033 (4)
C220.080 (4)0.054 (3)0.058 (3)0.000 (3)0.013 (3)−0.011 (2)
C230.106 (5)0.072 (4)0.062 (3)0.018 (3)0.017 (3)−0.024 (3)
C240.103 (5)0.057 (3)0.067 (3)0.023 (3)−0.013 (3)−0.026 (3)
C250.069 (3)0.041 (2)0.059 (3)0.007 (2)−0.020 (3)−0.013 (2)
C260.050 (3)0.037 (2)0.046 (2)0.0065 (19)−0.016 (2)−0.0072 (19)
C270.040 (3)0.034 (2)0.055 (3)−0.0003 (18)−0.009 (2)0.0014 (19)
C280.049 (3)0.045 (3)0.067 (3)−0.008 (2)−0.013 (2)0.009 (2)
C290.059 (3)0.060 (3)0.095 (4)−0.009 (3)0.003 (3)0.029 (3)
C300.060 (3)0.072 (3)0.080 (4)0.000 (3)0.027 (3)0.020 (3)
C310.067 (3)0.053 (3)0.062 (3)0.001 (2)0.021 (3)0.003 (2)
C320.091 (4)0.035 (2)0.095 (4)−0.002 (3)−0.033 (4)−0.010 (3)
C330.080 (4)0.038 (3)0.101 (4)−0.019 (3)−0.021 (3)0.011 (3)
O80.228 (6)0.099 (3)0.070 (3)0.078 (3)−0.047 (3)−0.014 (2)

Geometric parameters (Å, °)

Co1—O22.076 (3)C10—H10A0.9300
Co1—O42.106 (4)C11—C121.349 (8)
Co1—N52.130 (3)C11—H11A0.9300
Co1—N22.133 (3)C12—C131.386 (8)
Co1—N32.142 (3)C12—H12A0.9300
Co1—N42.173 (3)C13—C141.396 (6)
N1—C71.332 (6)C13—C201.434 (8)
N1—C81.453 (6)C14—C151.432 (6)
N1—H1G0.86 (7)C20—C211.340 (9)
N2—C101.335 (5)C20—H20A0.9300
N2—C141.345 (5)C15—C161.404 (6)
N3—C191.322 (5)C16—C171.385 (8)
N3—C151.363 (5)C16—C211.433 (8)
N4—C221.320 (5)C17—C181.362 (8)
N4—C261.352 (5)C17—H17A0.9300
N5—C311.324 (5)C18—C191.403 (7)
N5—C271.363 (5)C18—H18A0.9300
N6—O51.192 (6)C19—H19A0.9300
N6—O61.219 (5)C21—H21A0.9300
N6—O71.241 (6)C22—C231.383 (6)
O1—C71.230 (5)C22—H22A0.9300
O2—C91.248 (5)C23—C241.365 (7)
O3—C91.248 (5)C23—H23A0.9300
O4—H4F0.85 (7)C24—C251.395 (7)
O4—H4E0.87 (6)C24—H24A0.9300
C1—C21.386 (11)C25—C261.409 (6)
C1—C61.390 (8)C25—C321.430 (7)
C1—H1A0.9300C26—C271.442 (6)
C2—C31.342 (14)C27—C281.395 (6)
C2—H2A0.9300C28—C291.410 (7)
C3—C41.335 (13)C28—C331.423 (7)
C3—H3A0.9300C29—C301.348 (7)
C4—C51.403 (9)C29—H29A0.9300
C4—H4A0.9300C30—C311.396 (6)
C5—C61.384 (7)C30—H30A0.9300
C5—H5A0.9300C31—H31A0.9300
C6—C71.498 (7)C32—C331.339 (7)
C8—C91.524 (5)C32—H32A0.9300
C8—H8A0.9700C33—H33A0.9300
C8—H8B0.9700O8—H8F0.8504
C10—C111.412 (7)O8—H8E0.8689
O2—Co1—O486.91 (13)C12—C11—C10119.8 (5)
O2—Co1—N592.25 (12)C12—C11—H11A120.1
O4—Co1—N591.65 (14)C10—C11—H11A120.1
O2—Co1—N298.52 (12)C11—C12—C13119.6 (5)
O4—Co1—N295.91 (15)C11—C12—H12A120.2
N5—Co1—N2167.14 (13)C13—C12—H12A120.2
O2—Co1—N382.63 (12)C12—C13—C14117.9 (5)
O4—Co1—N3166.78 (13)C12—C13—C20122.8 (6)
N5—Co1—N396.80 (13)C14—C13—C20119.4 (6)
N2—Co1—N377.76 (13)N2—C14—C13123.0 (5)
O2—Co1—N4168.91 (12)N2—C14—C15117.9 (4)
O4—Co1—N496.67 (14)C13—C14—C15119.1 (5)
N5—Co1—N477.20 (13)C21—C20—C13121.0 (6)
N2—Co1—N491.57 (13)C21—C20—H20A119.5
N3—Co1—N495.12 (12)C13—C20—H20A119.5
C7—N1—C8119.9 (4)N3—C15—C16122.2 (4)
C7—N1—H1G126 (5)N3—C15—C14117.1 (4)
C8—N1—H1G111 (5)C16—C15—C14120.7 (4)
C10—N2—C14118.1 (4)C17—C16—C15118.1 (5)
C10—N2—Co1128.2 (3)C17—C16—C21123.8 (6)
C14—N2—Co1113.7 (3)C15—C16—C21118.1 (5)
C19—N3—C15117.9 (4)C18—C17—C16119.8 (5)
C19—N3—Co1128.5 (3)C18—C17—H17A120.1
C15—N3—Co1112.9 (3)C16—C17—H17A120.1
C22—N4—C26117.4 (4)C17—C18—C19119.0 (5)
C22—N4—Co1129.1 (3)C17—C18—H18A120.5
C26—N4—Co1113.5 (3)C19—C18—H18A120.5
C31—N5—C27117.8 (4)N3—C19—C18122.9 (5)
C31—N5—Co1127.3 (3)N3—C19—H19A118.5
C27—N5—Co1114.8 (3)C18—C19—H19A118.5
O5—N6—O6121.9 (6)C20—C21—C16121.6 (6)
O5—N6—O7120.0 (6)C20—C21—H21A119.2
O6—N6—O7118.0 (6)C16—C21—H21A119.2
C9—O2—Co1134.3 (3)N4—C22—C23123.6 (5)
Co1—O4—H4F96 (5)N4—C22—H22A118.2
Co1—O4—H4E126 (4)C23—C22—H22A118.2
H4F—O4—H4E99 (6)C24—C23—C22119.0 (5)
C2—C1—C6121.0 (8)C24—C23—H23A120.5
C2—C1—H1A119.5C22—C23—H23A120.5
C6—C1—H1A119.5C23—C24—C25120.2 (5)
C3—C2—C1119.6 (11)C23—C24—H24A119.9
C3—C2—H2A120.2C25—C24—H24A119.9
C1—C2—H2A120.2C24—C25—C26116.3 (5)
C4—C3—C2121.3 (11)C24—C25—C32124.7 (5)
C4—C3—H3A119.3C26—C25—C32119.0 (5)
C2—C3—H3A119.3N4—C26—C25123.5 (4)
C3—C4—C5120.9 (10)N4—C26—C27117.5 (4)
C3—C4—H4A119.5C25—C26—C27118.9 (4)
C5—C4—H4A119.5N5—C27—C28123.3 (4)
C6—C5—C4119.2 (7)N5—C27—C26116.9 (4)
C6—C5—H5A120.4C28—C27—C26119.8 (4)
C4—C5—H5A120.4C27—C28—C29116.5 (4)
C5—C6—C1118.0 (6)C27—C28—C33119.8 (5)
C5—C6—C7123.6 (5)C29—C28—C33123.7 (5)
C1—C6—C7118.4 (6)C30—C29—C28120.3 (5)
O1—C7—N1122.1 (5)C30—C29—H29A119.9
O1—C7—C6120.5 (5)C28—C29—H29A119.9
N1—C7—C6117.4 (4)C29—C30—C31119.5 (5)
N1—C8—C9114.0 (3)C29—C30—H30A120.2
N1—C8—H8A108.8C31—C30—H30A120.2
C9—C8—H8A108.8N5—C31—C30122.6 (5)
N1—C8—H8B108.8N5—C31—H31A118.7
C9—C8—H8B108.8C30—C31—H31A118.7
H8A—C8—H8B107.7C33—C32—C25121.7 (5)
O3—C9—O2126.5 (4)C33—C32—H32A119.1
O3—C9—C8115.8 (4)C25—C32—H32A119.1
O2—C9—C8117.7 (4)C32—C33—C28120.7 (5)
N2—C10—C11121.5 (5)C32—C33—H33A119.7
N2—C10—H10A119.3C28—C33—H33A119.7
C11—C10—H10A119.3H8F—O8—H8E119.3
O2—Co1—N2—C10105.1 (4)C11—C12—C13—C20177.3 (5)
O4—Co1—N2—C1017.4 (4)C10—N2—C14—C13−2.4 (6)
N5—Co1—N2—C10−108.3 (7)Co1—N2—C14—C13178.8 (3)
N3—Co1—N2—C10−174.4 (4)C10—N2—C14—C15178.0 (4)
N4—Co1—N2—C10−79.5 (4)Co1—N2—C14—C15−0.8 (5)
O2—Co1—N2—C14−76.3 (3)C12—C13—C14—N24.1 (7)
O4—Co1—N2—C14−164.0 (3)C20—C13—C14—N2−175.7 (4)
N5—Co1—N2—C1470.3 (7)C12—C13—C14—C15−176.3 (4)
N3—Co1—N2—C144.2 (3)C20—C13—C14—C153.9 (6)
N4—Co1—N2—C1499.1 (3)C12—C13—C20—C21179.6 (5)
O2—Co1—N3—C19−77.2 (3)C14—C13—C20—C21−0.6 (8)
O4—Co1—N3—C19−115.2 (7)C19—N3—C15—C16−0.5 (6)
N5—Co1—N3—C1914.2 (4)Co1—N3—C15—C16−172.1 (3)
N2—Co1—N3—C19−177.6 (4)C19—N3—C15—C14−179.3 (4)
N4—Co1—N3—C1991.9 (4)Co1—N3—C15—C149.1 (4)
O2—Co1—N3—C1593.3 (3)N2—C14—C15—N3−5.8 (5)
O4—Co1—N3—C1555.3 (7)C13—C14—C15—N3174.7 (4)
N5—Co1—N3—C15−175.3 (3)N2—C14—C15—C16175.4 (4)
N2—Co1—N3—C15−7.1 (3)C13—C14—C15—C16−4.2 (6)
N4—Co1—N3—C15−97.6 (3)N3—C15—C16—C170.6 (6)
O2—Co1—N4—C22160.5 (6)C14—C15—C16—C17179.4 (4)
O4—Co1—N4—C22−91.2 (4)N3—C15—C16—C21−177.6 (4)
N5—Co1—N4—C22178.6 (4)C14—C15—C16—C211.1 (6)
N2—Co1—N4—C224.9 (4)C15—C16—C17—C18−1.1 (7)
N3—Co1—N4—C2282.8 (4)C21—C16—C17—C18177.1 (5)
O2—Co1—N4—C26−20.5 (8)C16—C17—C18—C191.4 (8)
O4—Co1—N4—C2687.8 (3)C15—N3—C19—C180.8 (6)
N5—Co1—N4—C26−2.3 (3)Co1—N3—C19—C18170.9 (3)
N2—Co1—N4—C26−176.0 (3)C17—C18—C19—N3−1.3 (8)
N3—Co1—N4—C26−98.2 (3)C13—C20—C21—C16−2.5 (9)
O2—Co1—N5—C31−4.4 (4)C17—C16—C21—C20−175.9 (5)
O4—Co1—N5—C3182.6 (4)C15—C16—C21—C202.3 (8)
N2—Co1—N5—C31−151.3 (6)C26—N4—C22—C23−0.2 (7)
N3—Co1—N5—C31−87.2 (4)Co1—N4—C22—C23178.8 (4)
N4—Co1—N5—C31179.1 (4)N4—C22—C23—C24−0.3 (9)
O2—Co1—N5—C27179.4 (3)C22—C23—C24—C250.7 (8)
O4—Co1—N5—C27−93.6 (3)C23—C24—C25—C26−0.5 (7)
N2—Co1—N5—C2732.5 (8)C23—C24—C25—C32−179.1 (5)
N3—Co1—N5—C2796.6 (3)C22—N4—C26—C250.3 (6)
N4—Co1—N5—C272.8 (3)Co1—N4—C26—C25−178.8 (3)
O4—Co1—O2—C917.3 (4)C22—N4—C26—C27−179.3 (4)
N5—Co1—O2—C9108.9 (4)Co1—N4—C26—C271.6 (4)
N2—Co1—O2—C9−78.2 (4)C24—C25—C26—N40.0 (6)
N3—Co1—O2—C9−154.6 (4)C32—C25—C26—N4178.6 (4)
N4—Co1—O2—C9126.5 (7)C24—C25—C26—C27179.6 (4)
C6—C1—C2—C3−0.6 (13)C32—C25—C26—C27−1.8 (6)
C1—C2—C3—C40.6 (16)C31—N5—C27—C28−1.2 (6)
C2—C3—C4—C5−0.2 (15)Co1—N5—C27—C28175.4 (3)
C3—C4—C5—C6−0.1 (11)C31—N5—C27—C26−179.6 (4)
C4—C5—C6—C10.0 (8)Co1—N5—C27—C26−3.0 (5)
C4—C5—C6—C7−177.6 (5)N4—C26—C27—N50.9 (5)
C2—C1—C6—C50.4 (8)C25—C26—C27—N5−178.7 (4)
C2—C1—C6—C7178.1 (6)N4—C26—C27—C28−177.5 (4)
C8—N1—C7—O1−11.4 (6)C25—C26—C27—C282.8 (6)
C8—N1—C7—C6170.5 (4)N5—C27—C28—C290.8 (6)
C5—C6—C7—O1167.1 (5)C26—C27—C28—C29179.1 (4)
C1—C6—C7—O1−10.5 (7)N5—C27—C28—C33179.4 (4)
C5—C6—C7—N1−14.8 (7)C26—C27—C28—C33−2.3 (6)
C1—C6—C7—N1167.6 (4)C27—C28—C29—C30−0.4 (7)
C7—N1—C8—C9−77.2 (5)C33—C28—C29—C30−179.0 (5)
Co1—O2—C9—O3−4.7 (7)C28—C29—C30—C310.5 (8)
Co1—O2—C9—C8175.5 (3)C27—N5—C31—C301.3 (7)
N1—C8—C9—O3177.4 (4)Co1—N5—C31—C30−174.9 (4)
N1—C8—C9—O2−2.8 (6)C29—C30—C31—N5−1.0 (8)
C14—N2—C10—C11−0.8 (6)C24—C25—C32—C33178.6 (5)
Co1—N2—C10—C11177.8 (3)C26—C25—C32—C330.1 (7)
N2—C10—C11—C122.3 (8)C25—C32—C33—C280.5 (8)
C10—C11—C12—C13−0.6 (8)C27—C28—C33—C320.6 (7)
C11—C12—C13—C14−2.4 (8)C29—C28—C33—C32179.1 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O8—H8E···O50.872.463.084 (7)129
O8—H8E···O70.872.242.982 (7)143
O4—H4F···O20.85 (7)2.48 (7)2.876 (5)110 (5)
O4—H4F···O30.85 (7)1.87 (7)2.696 (5)162 (7)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2275).

References

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