Hexakis(4-nitro­pyridine N-oxide-κN¹)cobalt(II) bis­(perchlorate)

In the title complex, [Co(C₅H₄N₂O₃)₆](ClO₄)₂, six 4-nitro­pyridine N-oxide (npo) ligands coordinate to the Co^II atom via their N-oxide O atoms, resulting in an octa­hedral CoO₆ grouping. The Co^II ion occupies an inversion centre. A short contact of 2.841 (12) Å is observed between a pyridine N atom and a perchlorate O atom.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in solvent or counterion
• R factor = 0.067
• wR factor = 0.181
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  N4     ..  O11     ..       2.84 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent .........          3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      37.00 Perc.
PLAT430_ALERT_2_C Short Inter D...A Contact  O6     ..  O11     ..       2.88 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O9     ..  C8      ..       2.99 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      33.10 Deg.
              O11' -CL1  -O11     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.30 Deg.
              O13  -CL1  -O13'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      27.50 Deg.
              O10  -CL1  -O10'    1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

S1. Comment

Pyridine N-oxide and its derivatives can act as bridging ligands in polynuclear metal complexes (Watson, 1969) or as monodentate ligands in mononulear complexes (Shi et al., 2005). We report here the synthesis and structure of the title Co^II complex, (I), incorporating the 4-nitropridine N-oxide (npo) ligand.

The molecular structure of (I) is shown in Fig. 1. The Co^II ion assumes a slightly distorted (Table 1) CoO₆ octahedral coordination geometry from the N-oxide O atoms of six monodentate npo ligands. Atom Co1 occupies an inversion centre.

In the crystal structure of (I), a short N4···O11ⁱ [symmetry code: (i) = 3/2 − x, 1/2 + y, 1/2 − z] contact of 2.841 (12) Å is observed between an N-oxide N atom and a perchlorate O atom (sum of van der Waals radii = 3.07 Å). A Coulombic attraction between the formal positive charge of N4 and the partial negative charge of O11 may be responsible for this.

S2. Experimental

An aqueous solution (10 ml) of 4-nitropyridine N-oxide (0.3375 g, 2.41 mmol) was added to an aqueous solution (15 ml) of Co(ClO₄)₂·6H₂O (0.2932 g, 0.801 mmol) and the mixture was stirred for a few minutes. Red single crystals of (I) were obtained after the solution was allowed to stand at room temperature for two weeks.

S3. Refinement

Three of the perchlorate O atoms are disordered over two sites in a 0.601 (13):0.393 (13) ratio (sum constrained to unity). The disordered O atoms were refined isotropiclly. All H atoms were included in calculated positions and were included in the final cycles of refinement using a riding model [C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C)].

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. View of (I), showing 30% displacement ellipsoids for the non-H atoms. The Cl—O bonds of the disordered perchlorate O atoms are shown as dashed lines. Primed atoms are generated by the symmetry operation (1 − x, 1 − y, 1 − z).

Hexakis(4-nitropyridine N-oxide-κN¹)cobalt(II) bis(perchlorate)

Crystal data

[Co(C5H4N2O3)6](ClO4)2	F(000) = 1114
Mr = 1098.44	Dx = 1.732 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5735 reflections
a = 8.4969 (12) Å	θ = 2.6–28.0°
b = 13.6406 (19) Å	µ = 0.65 mm^−1
c = 18.179 (3) Å	T = 298 K
β = 91.005 (2)°	Prism, red
V = 2106.7 (5) Å^3	0.48 × 0.23 × 0.21 mm
Z = 2

Data collection

Bruker SMART CCD diffractometer	4487 independent reflections
Radiation source: fine-focus sealed tube	4006 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ϕ and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.747, Tmax = 0.876	k = −17→10
12139 measured reflections	l = −23→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.181	w = 1/[σ^2(Fo^2) + (0.0878P)^2 + 2.72P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
4487 reflections	Δρmax = 0.96 e Å^−3
323 parameters	Δρmin = −0.64 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0063 (12)

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Co1	0.5000	0.5000	0.5000	0.0321 (2)
O6	0.5252 (3)	0.52629 (19)	0.39059 (13)	0.0450 (6)
O7	0.7471 (3)	0.51029 (19)	0.51044 (14)	0.0449 (6)
O3	0.5233 (3)	0.34864 (18)	0.48048 (14)	0.0458 (6)
N4	0.4518 (3)	0.4836 (2)	0.33432 (14)	0.0337 (6)
N5	0.4418 (3)	0.2715 (2)	0.50272 (15)	0.0354 (6)
C8	0.3122 (4)	0.4018 (3)	0.21550 (18)	0.0373 (7)
C6	0.3420 (5)	0.5346 (3)	0.2968 (2)	0.0426 (8)
H5	0.3154	0.5975	0.3120	0.051*
C11	0.3512 (5)	0.2760 (3)	0.5627 (2)	0.0432 (8)
H9	0.3485	0.3329	0.5908	0.052*
C5	0.8603 (5)	0.3577 (3)	0.4986 (2)	0.0516 (9)
H2	0.8302	0.3424	0.5462	0.062*
N6	0.8268 (3)	0.4462 (2)	0.47047 (16)	0.0383 (6)
N3	0.2347 (4)	0.3554 (3)	0.15135 (17)	0.0517 (8)
C14	0.3705 (5)	0.1069 (3)	0.4820 (2)	0.0453 (9)
H11	0.3794	0.0490	0.4553	0.054*
O5	0.1277 (5)	0.3991 (3)	0.12130 (19)	0.0769 (11)
C13	0.2712 (4)	0.1129 (3)	0.5405 (2)	0.0417 (8)
C15	0.4566 (5)	0.1884 (3)	0.46376 (19)	0.0417 (8)
H12	0.5252	0.1860	0.4245	0.050*
C1	0.8697 (5)	0.4709 (3)	0.4022 (2)	0.0455 (8)
H3	0.8470	0.5332	0.3840	0.055*
N1	0.1692 (5)	0.0292 (3)	0.5570 (2)	0.0586 (9)
C10	0.4953 (5)	0.3935 (3)	0.3138 (2)	0.0420 (8)
H8	0.5727	0.3602	0.3406	0.050*
N2	1.0640 (4)	0.2419 (3)	0.3430 (3)	0.0690 (12)
C2	0.9472 (5)	0.4043 (3)	0.3592 (2)	0.0522 (10)
H4	0.9763	0.4205	0.3116	0.063*
C9	0.4257 (5)	0.3501 (3)	0.25314 (19)	0.0434 (8)
H7	0.4549	0.2876	0.2382	0.052*
C7	0.2686 (5)	0.4943 (3)	0.2360 (2)	0.0446 (8)
H6	0.1918	0.5288	0.2096	0.053*
C12	0.2630 (5)	0.1963 (3)	0.5818 (2)	0.0468 (9)
H10	0.1984	0.1989	0.6225	0.056*
O4	0.2809 (5)	0.2754 (3)	0.1327 (2)	0.0855 (12)
O2	0.0580 (5)	0.0442 (3)	0.5963 (3)	0.0915 (13)
O1	0.2008 (5)	−0.0497 (2)	0.5292 (2)	0.0830 (11)
O9	1.0813 (5)	0.2611 (3)	0.2787 (3)	0.1001 (15)
C4	0.9382 (5)	0.2897 (3)	0.4578 (3)	0.0562 (10)
H1	0.9623	0.2283	0.4772	0.067*
C3	0.9803 (4)	0.3141 (3)	0.3876 (2)	0.0494 (9)
O8	1.1109 (5)	0.1680 (3)	0.3734 (3)	0.1064 (16)
Cl1	0.67662 (12)	0.11903 (7)	0.27260 (6)	0.0518 (3)
O11	0.8207 (13)	0.0994 (9)	0.2384 (6)	0.079 (4)*	0.399 (13)
O11'	0.7986 (12)	0.0534 (9)	0.2631 (6)	0.115 (3)*	0.601 (13)
O10	0.6240 (15)	0.1537 (8)	0.2021 (6)	0.074 (3)*	0.399 (13)
O10'	0.5538 (9)	0.1341 (5)	0.2145 (3)	0.0673 (19)*	0.601 (13)
O12	0.7041 (5)	0.2011 (3)	0.3187 (3)	0.0981 (13)
O13	0.541 (3)	0.102 (2)	0.3076 (13)	0.183 (9)*	0.399 (13)
O13'	0.6015 (9)	0.0451 (6)	0.3185 (4)	0.086 (3)*	0.601 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0433 (4)	0.0284 (3)	0.0246 (3)	−0.0059 (2)	0.0014 (2)	−0.0057 (2)
O6	0.0665 (17)	0.0429 (14)	0.0256 (11)	−0.0212 (12)	0.0026 (11)	−0.0081 (10)
O7	0.0482 (14)	0.0444 (15)	0.0422 (14)	−0.0044 (11)	−0.0012 (11)	−0.0098 (11)
O3	0.0611 (16)	0.0305 (12)	0.0462 (14)	−0.0076 (11)	0.0165 (12)	−0.0058 (11)
N4	0.0448 (15)	0.0317 (14)	0.0247 (13)	−0.0093 (12)	0.0051 (11)	−0.0045 (10)
N5	0.0406 (15)	0.0298 (14)	0.0359 (14)	−0.0004 (12)	0.0001 (11)	−0.0030 (11)
C8	0.0450 (19)	0.0372 (17)	0.0295 (15)	−0.0080 (14)	0.0008 (13)	−0.0030 (13)
C6	0.056 (2)	0.0301 (16)	0.0417 (18)	−0.0003 (15)	0.0029 (16)	−0.0078 (14)
C11	0.057 (2)	0.0292 (17)	0.0440 (19)	−0.0006 (15)	0.0115 (16)	−0.0069 (14)
C5	0.053 (2)	0.051 (2)	0.050 (2)	−0.0029 (18)	−0.0016 (17)	0.0133 (18)
N6	0.0359 (14)	0.0368 (15)	0.0422 (15)	−0.0068 (12)	−0.0033 (12)	0.0018 (12)
N3	0.068 (2)	0.053 (2)	0.0336 (15)	−0.0134 (17)	−0.0078 (15)	−0.0053 (15)
C14	0.058 (2)	0.0312 (18)	0.047 (2)	0.0023 (16)	−0.0061 (17)	−0.0096 (15)
O5	0.092 (3)	0.075 (2)	0.062 (2)	−0.011 (2)	−0.0390 (19)	0.0014 (17)
C13	0.0434 (19)	0.0322 (17)	0.049 (2)	−0.0039 (14)	−0.0063 (15)	0.0058 (15)
C15	0.054 (2)	0.0332 (18)	0.0377 (17)	0.0020 (15)	0.0026 (15)	−0.0054 (14)
C1	0.044 (2)	0.043 (2)	0.049 (2)	−0.0024 (16)	0.0065 (16)	0.0116 (17)
N1	0.063 (2)	0.0436 (19)	0.069 (2)	−0.0110 (17)	−0.0052 (19)	0.0054 (18)
C10	0.049 (2)	0.0381 (18)	0.0392 (18)	0.0042 (15)	−0.0037 (15)	−0.0054 (14)
N2	0.0410 (19)	0.060 (2)	0.106 (4)	−0.0054 (18)	0.016 (2)	−0.022 (2)
C2	0.048 (2)	0.057 (2)	0.052 (2)	−0.0048 (18)	0.0135 (17)	0.0056 (19)
C9	0.057 (2)	0.0360 (18)	0.0369 (17)	0.0023 (16)	0.0002 (15)	−0.0125 (14)
C7	0.050 (2)	0.0406 (19)	0.043 (2)	0.0000 (16)	−0.0049 (16)	0.0014 (15)
C12	0.054 (2)	0.0399 (19)	0.047 (2)	−0.0015 (17)	0.0119 (17)	−0.0018 (16)
O4	0.125 (3)	0.068 (2)	0.063 (2)	0.004 (2)	−0.022 (2)	−0.0380 (18)
O2	0.074 (2)	0.072 (2)	0.129 (4)	−0.022 (2)	0.035 (2)	0.001 (2)
O1	0.112 (3)	0.0388 (17)	0.099 (3)	−0.0250 (19)	0.010 (2)	−0.0065 (18)
O9	0.113 (3)	0.076 (3)	0.114 (3)	−0.019 (2)	0.070 (3)	−0.023 (2)
C4	0.051 (2)	0.041 (2)	0.076 (3)	0.0033 (18)	−0.002 (2)	0.011 (2)
C3	0.0309 (17)	0.047 (2)	0.070 (3)	−0.0039 (16)	0.0031 (16)	−0.0067 (19)
O8	0.096 (3)	0.084 (3)	0.138 (4)	0.049 (3)	−0.019 (3)	−0.029 (3)
Cl1	0.0539 (6)	0.0474 (6)	0.0542 (6)	0.0061 (4)	0.0088 (4)	−0.0148 (4)
O12	0.106 (3)	0.082 (3)	0.107 (3)	0.002 (2)	0.000 (2)	−0.044 (2)

Geometric parameters (Å, º)

Co1—O6^i	2.036 (2)	C14—H11	0.9300
Co1—O6	2.036 (2)	C13—C12	1.367 (5)
Co1—O3^i	2.105 (2)	C13—N1	1.467 (5)
Co1—O3	2.105 (2)	C15—H12	0.9300
Co1—O7^i	2.109 (3)	C1—C2	1.374 (6)
Co1—O7	2.109 (3)	C1—H3	0.9300
O6—N4	1.324 (3)	N1—O2	1.212 (5)
O7—N6	1.330 (4)	N1—O1	1.220 (5)
O3—N5	1.327 (4)	C10—C9	1.376 (5)
N4—C10	1.337 (4)	C10—H8	0.9300
N4—C6	1.341 (5)	N2—O9	1.210 (6)
N5—C15	1.344 (4)	N2—O8	1.214 (6)
N5—C11	1.347 (4)	N2—C3	1.468 (6)
C8—C9	1.368 (5)	C2—C3	1.363 (6)
C8—C7	1.369 (5)	C2—H4	0.9300
C8—N3	1.472 (4)	C9—H7	0.9300
C6—C7	1.375 (5)	C7—H6	0.9300
C6—H5	0.9300	C12—H10	0.9300
C11—C12	1.369 (5)	C4—C3	1.372 (6)
C11—H9	0.9300	C4—H1	0.9300
C5—N6	1.340 (5)	Cl1—O13	1.35 (2)
C5—C4	1.366 (6)	Cl1—O11'	1.383 (10)
C5—H2	0.9300	Cl1—O11	1.409 (11)
N6—C1	1.343 (5)	Cl1—O12	1.416 (4)
N3—O5	1.209 (5)	Cl1—O10	1.431 (10)
N3—O4	1.211 (5)	Cl1—O13'	1.463 (8)
C14—C13	1.371 (6)	Cl1—O10'	1.486 (6)
C14—C15	1.375 (5)
O6^i—Co1—O6	180.0	N6—C1—C2	120.0 (4)
O6^i—Co1—O3^i	89.79 (10)	N6—C1—H3	120.0
O6—Co1—O3^i	90.21 (10)	C2—C1—H3	120.0
O6^i—Co1—O3	90.21 (10)	O2—N1—O1	124.9 (4)
O6—Co1—O3	89.79 (10)	O2—N1—C13	117.3 (4)
O3^i—Co1—O3	180.0	O1—N1—C13	117.8 (4)
O6^i—Co1—O7^i	87.39 (11)	N4—C10—C9	120.1 (3)
O6—Co1—O7^i	92.61 (11)	N4—C10—H8	119.9
O3^i—Co1—O7^i	89.09 (10)	C9—C10—H8	119.9
O3—Co1—O7^i	90.91 (10)	O9—N2—O8	125.2 (5)
O6^i—Co1—O7	92.61 (11)	O9—N2—C3	117.2 (5)
O6—Co1—O7	87.39 (11)	O8—N2—C3	117.6 (5)
O3^i—Co1—O7	90.91 (10)	C3—C2—C1	118.6 (4)
O3—Co1—O7	89.09 (10)	C3—C2—H4	120.7
O7^i—Co1—O7	180.0	C1—C2—H4	120.7
Co1—O6—N4	128.39 (19)	C8—C9—C10	117.9 (3)
Co1—O7—N6	115.01 (19)	C8—C9—H7	121.1
Co1—O3—N5	132.5 (2)	C10—C9—H7	121.1
O6—N4—C10	119.4 (3)	C8—C7—C6	117.8 (4)
O6—N4—C6	118.6 (3)	C8—C7—H6	121.1
C10—N4—C6	121.9 (3)	C6—C7—H6	121.1
O3—N5—C15	117.0 (3)	C13—C12—C11	119.2 (3)
O3—N5—C11	121.3 (3)	C13—C12—H10	120.4
C15—N5—C11	121.7 (3)	C11—C12—H10	120.4
C9—C8—C7	122.1 (3)	C5—C4—C3	118.5 (4)
C9—C8—N3	118.4 (3)	C5—C4—H1	120.8
C7—C8—N3	119.5 (3)	C3—C4—H1	120.8
N4—C6—C7	120.2 (3)	C2—C3—C4	121.1 (4)
N4—C6—H5	119.9	C2—C3—N2	119.7 (4)
C7—C6—H5	119.9	C4—C3—N2	119.2 (4)
N5—C11—C12	119.5 (3)	O13—Cl1—O11'	126.7 (15)
N5—C11—H9	120.2	O13—Cl1—O11	159.1 (14)
C12—C11—H9	120.2	O11'—Cl1—O11	33.1 (5)
N6—C5—C4	120.5 (4)	O13—Cl1—O12	89.4 (10)
N6—C5—H2	119.8	O11'—Cl1—O12	118.0 (5)
C4—C5—H2	119.8	O11—Cl1—O12	106.1 (5)
O7—N6—C5	119.4 (3)	O13—Cl1—O10	102.9 (11)
O7—N6—C1	119.3 (3)	O11'—Cl1—O10	109.0 (7)
C5—N6—C1	121.3 (3)	O11—Cl1—O10	85.9 (8)
O5—N3—O4	124.2 (4)	O12—Cl1—O10	108.3 (5)
O5—N3—C8	117.9 (4)	O13—Cl1—O13'	39.3 (11)
O4—N3—C8	117.8 (4)	O11'—Cl1—O13'	87.7 (7)
C13—C14—C15	118.4 (3)	O11—Cl1—O13'	120.8 (7)
C13—C14—H11	120.8	O12—Cl1—O13'	106.1 (4)
C15—C14—H11	120.8	O10—Cl1—O13'	127.3 (6)
C12—C13—C14	120.9 (3)	O13—Cl1—O10'	76.3 (10)
C12—C13—N1	120.0 (4)	O11'—Cl1—O10'	121.3 (5)
C14—C13—N1	119.1 (3)	O11—Cl1—O10'	108.5 (6)
N5—C15—C14	120.0 (3)	O12—Cl1—O10'	114.7 (3)
N5—C15—H12	120.0	O10—Cl1—O10'	27.5 (4)
C14—C15—H12	120.0	O13'—Cl1—O10'	101.1 (4)
O3^i—Co1—O6—N4	−131.1 (3)	O3—N5—C15—C14	−177.3 (3)
O3—Co1—O6—N4	48.9 (3)	C11—N5—C15—C14	4.2 (6)
O7^i—Co1—O6—N4	−42.0 (3)	C13—C14—C15—N5	−0.3 (6)
O7—Co1—O6—N4	138.0 (3)	O7—N6—C1—C2	−177.6 (3)
O6^i—Co1—O7—N6	120.7 (2)	C5—N6—C1—C2	1.2 (6)
O6—Co1—O7—N6	−59.3 (2)	C12—C13—N1—O2	15.5 (6)
O3^i—Co1—O7—N6	−149.5 (2)	C14—C13—N1—O2	−162.6 (4)
O3—Co1—O7—N6	30.5 (2)	C12—C13—N1—O1	−165.6 (4)
O6^i—Co1—O3—N5	46.9 (3)	C14—C13—N1—O1	16.3 (6)
O6—Co1—O3—N5	−133.1 (3)	O6—N4—C10—C9	−176.7 (3)
O7^i—Co1—O3—N5	−40.5 (3)	C6—N4—C10—C9	−0.7 (5)
O7—Co1—O3—N5	139.5 (3)	N6—C1—C2—C3	−0.7 (6)
Co1—O6—N4—C10	−76.4 (4)	C7—C8—C9—C10	0.7 (6)
Co1—O6—N4—C6	107.5 (3)	N3—C8—C9—C10	−178.8 (3)
Co1—O3—N5—C15	160.6 (3)	N4—C10—C9—C8	−0.1 (6)
Co1—O3—N5—C11	−20.9 (5)	C9—C8—C7—C6	−0.5 (6)
O6—N4—C6—C7	177.0 (3)	N3—C8—C7—C6	179.1 (3)
C10—N4—C6—C7	1.0 (5)	N4—C6—C7—C8	−0.4 (6)
O3—N5—C11—C12	176.9 (3)	C14—C13—C12—C11	2.5 (6)
C15—N5—C11—C12	−4.6 (6)	N1—C13—C12—C11	−175.6 (4)
Co1—O7—N6—C5	−87.9 (3)	N5—C11—C12—C13	1.3 (6)
Co1—O7—N6—C1	90.9 (3)	N6—C5—C4—C3	−0.4 (6)
C4—C5—N6—O7	178.2 (4)	C1—C2—C3—C4	−0.2 (6)
C4—C5—N6—C1	−0.6 (6)	C1—C2—C3—N2	−179.5 (4)
C9—C8—N3—O5	175.4 (4)	C5—C4—C3—C2	0.8 (6)
C7—C8—N3—O5	−4.2 (5)	C5—C4—C3—N2	−179.9 (4)
C9—C8—N3—O4	−3.7 (6)	O9—N2—C3—C2	−9.9 (6)
C7—C8—N3—O4	176.7 (4)	O8—N2—C3—C2	169.8 (4)
C15—C14—C13—C12	−2.9 (6)	O9—N2—C3—C4	170.8 (4)
C15—C14—C13—N1	175.1 (3)	O8—N2—C3—C4	−9.5 (6)

Symmetry code: (i) −x+1, −y+1, −z+1.