[2-(N,N-Di­methyl­carbamoyl)­ethyl]­bis­(di­methyl­glyoximato)[(R)-1-phenyl­ethyl­amine]­cobalt(III)

The 2-(N,N-di­methyl­carbamoyl)­ethyl group of the title complex, [Co(C₄H₇N₂O₂)₂(C₅H₁₀NO)(C₈H₁₁N)], forms a hydrogen bond with the (R)-1-phenyl­ethyl­amine group of a neighboring mol­ecule, which may be a reason why the group gave low reactivity in the solid-state photoisomerization to 1-(N,N-di­methyl­carbamoyl)­ethyl group.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.045
• wR factor = 0.122
• Data-to-parameter ratio = 9.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



WEIGH_01  Alert C Extra text has been found in the
          _refine_ls_weighting_scheme field. This should be in the
          _refine_ls_weighting_details field.
          Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0846P)^2^] wher
          Weighting scheme identified as calc

PLAT_420  Alert C D-H without acceptor       N6     -   H06A              ?

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.50
         From the CIF: _reflns_number_total               3061
         Count of symmetry unique reflns         3061
         Completeness (_total/calc)            100.00%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

S1. Comment

A series of cobaloxime complexes containing the 2-(N-substituted-carbamoyl)ethyl group were synthesized to analyze the relationship between the void space and the intermolecular hydrogen bond (Ohgo et al., 1996, 2001), since the 2-carbamoylethyl group has both the hydrogen-donor (NH) and acceptor (C═O) atoms. In the course of the studies on photoracemization and (β–α) photoisomerization in a series of cobaloxime complexes, the 2-substituted-carbamoylethyl groups in some cobaloxime complexes were found to be isomerized to the 1-substituted-carbamoylethyl groups. Futhermore, asymmetric induction up to 69% ee was observed in the photoreaction of the above complexes. In terms of this asymmetric induction, the hydrogen bonds of the reactive groups may play a role. The title compound, (I), was synthesized to make clear the role of hydrogen bonds in the solid-state photoreaction, systematically.

The crystal structures of (I) viewed along the a axis is shown in Fig. 1 and Fig. 2 shows the molecule of (I) with the numbering of the atoms. The trans conformations around Co—C9—C10—N5 and C10—C11—N5—C12 indicate that the 2-(N,N-dimethylcarbamoyl)ethyl group lies perpendicular to the cobaloxime plane·The torsion angle C9—C10—C11—N5, 78.8°, is almost the same angle as that in bis(dimethylglyoximato)[2-(methylcarbamoyl)ethyl][methyl (S)-phenylalaninate]cobalt(III), 75.0° (Ohgo et al., 2000). The hydrogen bonds in (I) are given in Table 2. The N6 atom of the (R)-1-phenylethylamine moiety is hydrogen bonded to the O5 atom of the 2-(N,N-dimethylcarbamoyl)ethyl moiety of the neighboring molecule at (-x, y - 1/2, -z). Further investigation on the correlation between the structure and the reactivity is in progress.

S2. Experimental

The preparation of (I) were carried out according to literature methods with minor changes (Ohgo et al., 1996). Crystals were obtained by recrystallization from ethanol/hexane.

S3. Refinement

The H atoms were refined using a riding model. The positional parameters of the H atoms were constrained to have C—H distances of 0.96 Å for primary, 0.97 Å for secondary, and 0.93 Å for aromatic. H-atom U values were constrained to 1.2 times the U_eq of the atoms to which they are attached (1.5 for methyl groups). The absolute configuration of (I) was set by reference to the known absolute configurations of the chiral amino ligands. There were no Friedel pairs in the measured data.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1992b); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The crystal structure of the title compound viewed along the a axis. Dotted lines show the hydrogen bonds.
	Fig. 2. The molecular structure of the title compound with the atomic numbering. Displacement ellipsoids are shown at the 50% probability level and H atoms have been omitted.

Bis(dimethylglyoximato)[2,2-(dimethylcarbamoyl)ethyl] [(R)-1-phenylethylamine]cobalt(III)

Crystal data

[Co(C4H7N2O2)2(C5H10NO)(C8H11N)]	F(000) = 540
Mr = 510.48	Dx = 1.325 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.8987 (13) Å	Cell parameters from 25 reflections
b = 14.3050 (16) Å	θ = 12.5–15.0°
c = 10.1286 (11) Å	µ = 0.71 mm^−1
β = 97.096 (9)°	T = 298 K
V = 1279.5 (3) Å^3	Prismatic, red
Z = 2	0.20 × 0.10 × 0.05 mm

Data collection

Rigaku AFC5 diffractometer	2589 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 2.0°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→18
Tmin = 0.871, Tmax = 0.965	l = −13→13
3061 measured reflections	3 standard reflections every 100 reflections
3061 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.02	Calculated w = 1/[σ^2(Fo^2) + (0.0846P)^2] where P = (Fo^2 + 2Fc^2)/3
3061 reflections	(Δ/σ)max < 0.001
309 parameters	Δρmax = 0.83 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

Special details

Experimental. Bis(dimethylglyoximato)[2,2-(dimethylcarbamoyl)ethyl] [(R)-1-phenylethylamine]cobalt(III) The preparation of the series of N-substituted cobaloxime complexes was basically carried out according to the literature methods with minor change·(Ohgo et al., 1996) The crystal were obtained by slow evaporation from ethanol/hexane.

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
Co1	0.23975 (5)	−0.0004 (5)	0.06825 (5)	0.03753 (15)
O1	0.3063 (4)	−0.1065 (3)	−0.1544 (4)	0.0684 (11)
H01	0.3884	−0.0616	−0.1158	0.082*
O2	−0.0314 (4)	0.0012 (5)	0.1904 (3)	0.0693 (9)
O3	0.1719 (4)	0.1073 (3)	0.2890 (3)	0.0686 (10)
H03	0.0896	0.0644	0.2492	0.082*
O4	0.5067 (3)	0.0033 (5)	−0.0605 (3)	0.0662 (8)
O5	−0.1023 (6)	0.2371 (4)	−0.2033 (5)	0.0918 (15)
N1	0.2041 (5)	−0.0878 (3)	−0.0702 (5)	0.0447 (10)
N2	0.0420 (4)	−0.0343 (3)	0.0925 (4)	0.0490 (9)
N3	0.2743 (6)	0.0895 (4)	0.2055 (5)	0.0509 (11)
N4	0.4345 (4)	0.0381 (3)	0.0387 (4)	0.0494 (9)
N5	0.0416 (6)	0.1771 (5)	−0.3478 (5)	0.0812 (16)
N6	0.3110 (6)	−0.1056 (4)	0.2008 (6)	0.0629 (15)
H06A	0.2679	−0.0942	0.2750	0.076*
H06B	0.2690	−0.1588	0.1660	0.076*
C1	0.0733 (6)	−0.1273 (4)	−0.0864 (6)	0.0520 (11)
C2	−0.0239 (5)	−0.0962 (4)	0.0119 (5)	0.0516 (11)
C3	0.4012 (7)	0.1340 (4)	0.2141 (6)	0.0583 (13)
C4	0.4968 (6)	0.1047 (4)	0.1148 (6)	0.0565 (12)
C5	0.0235 (8)	−0.1939 (5)	−0.1949 (7)	0.082 (2)
H5A	−0.0557	−0.1661	−0.2551	0.123*
H5B	−0.0137	−0.2499	−0.1579	0.123*
H5C	0.1075	−0.2090	−0.2420	0.123*
C6	−0.1826 (6)	−0.1312 (5)	0.0181 (8)	0.083 (2)
H6A	−0.2194	−0.1611	−0.0644	0.125*
H6B	−0.2472	−0.0795	0.0329	0.125*
H6C	−0.1822	−0.1752	0.0896	0.125*
C7	0.4475 (10)	0.2073 (6)	0.3181 (8)	0.095 (2)
H7A	0.4641	0.2656	0.2754	0.142*
H7B	0.5392	0.1881	0.3713	0.142*
H7C	0.3687	0.2148	0.3740	0.142*
C8	0.6471 (7)	0.1470 (5)	0.0981 (8)	0.084 (2)
H8A	0.7264	0.1102	0.1454	0.126*
H8B	0.6516	0.2095	0.1328	0.126*
H8C	0.6597	0.1485	0.0053	0.126*
C9	0.1624 (7)	0.1007 (4)	−0.0599 (6)	0.0531 (14)
H9A	0.1617	0.1582	−0.0092	0.064*
H9B	0.2369	0.1088	−0.1213	0.064*
C10	0.0104 (6)	0.0930 (4)	−0.1423 (6)	0.0581 (12)
H10A	−0.0678	0.0898	−0.0837	0.070*
H10B	0.0067	0.0356	−0.1936	0.070*
C11	−0.0212 (6)	0.1745 (4)	−0.2355 (5)	0.0563 (13)
C12	0.0138 (12)	0.2548 (9)	−0.4355 (9)	0.157 (5)
H12A	−0.0765	0.2437	−0.4956	0.235*
H12B	0.0980	0.2628	−0.4852	0.235*
H12C	0.0012	0.3103	−0.3846	0.235*
C13	0.1366 (10)	0.1020 (9)	−0.3919 (7)	0.114 (3)
H13A	0.2342	0.1268	−0.4041	0.171*
H13B	0.0893	0.0767	−0.4745	0.171*
H13C	0.1483	0.0536	−0.3259	0.171*
C20	0.4746 (6)	−0.1275 (4)	0.2457 (6)	0.0559 (13)
H20	0.5341	−0.1088	0.1748	0.067*
C21	0.5321 (5)	−0.0738 (4)	0.3693 (4)	0.0492 (10)
C22	0.6699 (7)	−0.0306 (5)	0.3788 (8)	0.087 (2)
H22	0.7252	−0.0324	0.3067	0.105*
C23	0.7297 (10)	0.0166 (8)	0.4953 (13)	0.128 (4)
H23	0.8234	0.0460	0.4993	0.154*
C24	0.6527 (14)	0.0194 (10)	0.6001 (11)	0.144 (5)
H24	0.6934	0.0500	0.6773	0.173*
C25	0.5185 (12)	−0.0212 (8)	0.5945 (7)	0.112 (4)
H25	0.4649	−0.0178	0.6676	0.135*
C26	0.4553 (7)	−0.0696 (6)	0.4800 (6)	0.083 (2)
H26	0.3617	−0.0988	0.4787	0.100*
C27	0.4963 (12)	−0.2332 (5)	0.2690 (9)	0.113 (3)
H27A	0.6021	−0.2467	0.2907	0.170*
H27B	0.4574	−0.2664	0.1897	0.170*
H27C	0.4427	−0.2524	0.3411	0.170*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0378 (2)	0.0401 (2)	0.0339 (2)	0.0007 (3)	0.00110 (15)	0.0006 (3)
O1	0.073 (2)	0.068 (3)	0.068 (3)	0.0005 (19)	0.0250 (19)	−0.023 (2)
O2	0.0573 (17)	0.085 (2)	0.071 (2)	0.000 (3)	0.0286 (15)	−0.004 (4)
O3	0.083 (2)	0.079 (3)	0.0441 (19)	0.008 (2)	0.0120 (17)	−0.0153 (19)
O4	0.0540 (16)	0.073 (2)	0.077 (2)	0.005 (3)	0.0276 (15)	−0.003 (3)
O5	0.098 (3)	0.076 (3)	0.097 (3)	0.041 (3)	−0.005 (3)	−0.002 (3)
N1	0.045 (2)	0.045 (2)	0.044 (2)	0.0074 (18)	0.0025 (17)	−0.0048 (17)
N2	0.0421 (18)	0.058 (2)	0.048 (2)	0.0009 (16)	0.0082 (16)	0.0021 (17)
N3	0.063 (3)	0.052 (2)	0.036 (2)	0.003 (2)	0.0026 (19)	0.0016 (19)
N4	0.0427 (18)	0.052 (2)	0.053 (2)	0.0022 (16)	0.0055 (16)	0.0074 (18)
N5	0.081 (3)	0.117 (5)	0.044 (2)	0.009 (3)	0.005 (2)	0.018 (3)
N6	0.058 (3)	0.057 (3)	0.068 (3)	−0.013 (2)	−0.015 (2)	0.026 (3)
C1	0.051 (3)	0.040 (2)	0.061 (3)	0.003 (2)	−0.007 (2)	−0.002 (2)
C2	0.043 (2)	0.046 (2)	0.063 (3)	−0.0010 (19)	−0.003 (2)	0.007 (2)
C3	0.071 (4)	0.047 (3)	0.051 (3)	−0.003 (3)	−0.015 (3)	−0.003 (2)
C4	0.052 (2)	0.046 (3)	0.068 (3)	−0.010 (2)	−0.006 (2)	0.006 (2)
C5	0.080 (4)	0.065 (4)	0.094 (5)	−0.004 (3)	−0.017 (4)	−0.036 (4)
C6	0.041 (3)	0.077 (4)	0.130 (6)	−0.009 (3)	0.003 (3)	−0.004 (4)
C7	0.116 (6)	0.077 (5)	0.084 (5)	−0.017 (4)	−0.017 (4)	−0.033 (4)
C8	0.058 (3)	0.074 (4)	0.117 (6)	−0.024 (3)	0.001 (3)	0.007 (4)
C9	0.060 (3)	0.046 (3)	0.050 (3)	0.000 (2)	−0.007 (2)	0.004 (2)
C10	0.051 (2)	0.064 (3)	0.058 (3)	0.012 (2)	0.002 (2)	0.014 (3)
C11	0.055 (3)	0.059 (3)	0.052 (3)	0.010 (2)	−0.009 (2)	0.001 (2)
C12	0.149 (9)	0.198 (12)	0.113 (7)	−0.039 (9)	−0.029 (6)	0.103 (8)
C13	0.111 (6)	0.172 (10)	0.061 (4)	0.018 (6)	0.015 (4)	−0.027 (5)
C20	0.059 (3)	0.053 (3)	0.053 (3)	0.008 (2)	−0.007 (2)	0.002 (2)
C21	0.050 (2)	0.052 (2)	0.044 (2)	0.009 (2)	−0.0034 (18)	0.006 (2)
C22	0.056 (3)	0.103 (6)	0.099 (5)	−0.008 (3)	−0.005 (3)	−0.004 (4)
C23	0.092 (5)	0.117 (9)	0.160 (9)	−0.015 (6)	−0.052 (6)	−0.021 (8)
C24	0.140 (9)	0.171 (13)	0.105 (7)	0.039 (9)	−0.049 (6)	−0.053 (9)
C25	0.144 (8)	0.140 (10)	0.051 (3)	0.044 (7)	0.004 (4)	−0.009 (4)
C26	0.076 (4)	0.116 (6)	0.059 (3)	0.004 (4)	0.017 (3)	0.008 (4)
C27	0.141 (8)	0.059 (4)	0.122 (7)	0.017 (4)	−0.055 (6)	−0.018 (5)

Geometric parameters (Å, º)

Co1—N2	1.871 (4)	C6—H6C	0.960
Co1—N1	1.876 (5)	C7—H7A	0.960
Co1—N4	1.878 (4)	C7—H7B	0.960
Co1—N3	1.891 (5)	C7—H7C	0.960
Co1—C9	2.008 (6)	C8—H8A	0.960
Co1—N6	2.065 (5)	C8—H8B	0.960
O1—N1	1.348 (6)	C8—H8C	0.960
O1—H01	1.014	C9—C10	1.503 (7)
O2—N2	1.352 (5)	C9—H9A	0.970
O2—H03	1.474	C9—H9B	0.970
O3—N3	1.342 (6)	C10—C11	1.505 (8)
O3—H03	1.001	C10—H10A	0.970
O4—N4	1.352 (5)	C10—H10B	0.970
O4—H01	1.462	C12—H12A	0.960
O5—C11	1.220 (7)	C12—H12B	0.960
N1—C1	1.286 (7)	C12—H12C	0.960
N2—C2	1.295 (6)	C13—H13A	0.960
N3—C3	1.290 (8)	C13—H13B	0.960
N4—C4	1.305 (7)	C13—H13C	0.960
N5—C11	1.328 (8)	C20—C21	1.503 (7)
N5—C12	1.425 (11)	C20—C27	1.539 (9)
N5—C13	1.470 (11)	C20—H20	0.980
N6—C20	1.504 (7)	C21—C22	1.366 (8)
N6—H06A	0.900	C21—C26	1.385 (8)
N6—H06B	0.900	C22—C23	1.406 (13)
C1—C2	1.467 (8)	C22—H22	0.930
C1—C5	1.481 (8)	C23—C24	1.333 (15)
C2—C6	1.506 (7)	C23—H23	0.930
C3—C4	1.456 (9)	C24—C25	1.323 (15)
C3—C7	1.507 (8)	C24—H24	0.930
C4—C8	1.497 (7)	C25—C26	1.407 (11)
C5—H5A	0.960	C25—H25	0.930
C5—H5B	0.960	C26—H26	0.930
C5—H5C	0.960	C27—H27A	0.960
C6—H6A	0.960	C27—H27B	0.960
C6—H6B	0.960	C27—H27C	0.960
N2—Co1—N1	81.4 (2)	C3—C7—H7C	109.5
N2—Co1—N4	177.3 (2)	H7A—C7—H7C	109.5
N1—Co1—N4	98.7 (2)	H7B—C7—H7C	109.5
N2—Co1—N3	98.6 (2)	C4—C8—H8A	109.5
N1—Co1—N3	178.9 (2)	C4—C8—H8B	109.5
N4—Co1—N3	81.3 (2)	H8A—C8—H8B	109.5
N2—Co1—C9	91.1 (2)	C4—C8—H8C	109.5
N1—Co1—C9	89.1 (2)	H8A—C8—H8C	109.5
N4—Co1—C9	86.3 (2)	H8B—C8—H8C	109.5
N3—Co1—C9	89.8 (3)	C10—C9—Co1	121.3 (4)
N2—Co1—N6	86.8 (2)	C10—C9—H9A	107.0
N1—Co1—N6	90.6 (2)	Co1—C9—H9A	107.0
N4—Co1—N6	95.9 (2)	C10—C9—H9B	107.0
N3—Co1—N6	90.5 (2)	Co1—C9—H9B	107.0
C9—Co1—N6	177.8 (3)	H9A—C9—H9B	106.7
N1—O1—H01	98.1	C9—C10—C11	112.1 (5)
N2—O2—H03	97.6	C9—C10—H10A	109.2
N3—O3—H03	98.6	C11—C10—H10A	109.2
N4—O4—H01	97.6	C9—C10—H10B	109.2
C1—N1—O1	120.2 (5)	C11—C10—H10B	109.2
C1—N1—Co1	117.1 (4)	H10A—C10—H10B	107.9
O1—N1—Co1	122.7 (4)	O5—C11—N5	122.3 (6)
C2—N2—O2	119.8 (4)	O5—C11—C10	118.1 (5)
C2—N2—Co1	117.1 (3)	N5—C11—C10	119.6 (5)
O2—N2—Co1	123.1 (3)	N5—C12—H12A	109.5
C3—N3—O3	121.4 (5)	N5—C12—H12B	109.5
C3—N3—Co1	116.5 (4)	H12A—C12—H12B	109.5
O3—N3—Co1	122.1 (4)	N5—C12—H12C	109.5
C4—N4—O4	120.1 (4)	H12A—C12—H12C	109.5
C4—N4—Co1	116.9 (4)	H12B—C12—H12C	109.5
O4—N4—Co1	122.9 (3)	N5—C13—H13A	109.5
C11—N5—C12	119.7 (8)	N5—C13—H13B	109.5
C11—N5—C13	123.9 (7)	H13A—C13—H13B	109.5
C12—N5—C13	116.3 (7)	N5—C13—H13C	109.5
C20—N6—Co1	123.8 (4)	H13A—C13—H13C	109.5
C20—N6—H06A	106.4	H13B—C13—H13C	109.5
Co1—N6—H06A	106.4	C21—C20—N6	111.3 (5)
C20—N6—H06B	106.4	C21—C20—C27	110.5 (5)
Co1—N6—H06B	106.4	N6—C20—C27	110.4 (6)
H06A—N6—H06B	106.5	C21—C20—H20	108.2
N1—C1—C2	112.4 (5)	N6—C20—H20	108.2
N1—C1—C5	124.1 (6)	C27—C20—H20	108.2
C2—C1—C5	123.4 (5)	C22—C21—C26	116.9 (6)
N2—C2—C1	112.1 (4)	C22—C21—C20	120.0 (5)
N2—C2—C6	123.7 (5)	C26—C21—C20	123.1 (5)
C1—C2—C6	124.2 (5)	C21—C22—C23	121.3 (8)
N3—C3—C4	113.1 (5)	C21—C22—H22	119.3
N3—C3—C7	123.5 (6)	C23—C22—H22	119.3
C4—C3—C7	123.4 (6)	C24—C23—C22	120.2 (9)
N4—C4—C3	112.1 (4)	C24—C23—H23	119.9
N4—C4—C8	123.3 (6)	C22—C23—H23	119.9
C3—C4—C8	124.6 (5)	C25—C24—C23	120.2 (9)
C1—C5—H5A	109.5	C25—C24—H24	119.9
C1—C5—H5B	109.5	C23—C24—H24	119.9
H5A—C5—H5B	109.5	C24—C25—C26	121.2 (8)
C1—C5—H5C	109.5	C24—C25—H25	119.4
H5A—C5—H5C	109.5	C26—C25—H25	119.4
H5B—C5—H5C	109.5	C21—C26—C25	120.1 (7)
C2—C6—H6A	109.5	C21—C26—H26	119.9
C2—C6—H6B	109.5	C25—C26—H26	119.9
H6A—C6—H6B	109.5	C20—C27—H27A	109.5
C2—C6—H6C	109.5	C20—C27—H27B	109.5
H6A—C6—H6C	109.5	H27A—C27—H27B	109.5
H6B—C6—H6C	109.5	C20—C27—H27C	109.5
C3—C7—H7A	109.5	H27A—C27—H27C	109.5
C3—C7—H7B	109.5	H27B—C27—H27C	109.5
H7A—C7—H7B	109.5
N2—Co1—N1—C1	0.6 (4)	Co1—N2—C2—C6	179.9 (5)
N4—Co1—N1—C1	−176.7 (4)	N1—C1—C2—N2	1.2 (7)
C9—Co1—N1—C1	−90.6 (5)	C5—C1—C2—N2	−176.6 (5)
N6—Co1—N1—C1	87.3 (4)	N1—C1—C2—C6	−179.5 (5)
N2—Co1—N1—O1	177.6 (4)	C5—C1—C2—C6	2.7 (9)
N4—Co1—N1—O1	0.3 (4)	Co1—N3—C3—C4	−0.8 (6)
C9—Co1—N1—O1	86.4 (4)	O3—N3—C3—C7	1.2 (9)
N6—Co1—N1—O1	−95.7 (4)	Co1—N3—C3—C7	−179.5 (5)
N1—Co1—N2—C2	0.1 (4)	O4—N4—C4—C3	179.0 (4)
N3—Co1—N2—C2	179.0 (4)	Co1—N4—C4—C3	2.3 (6)
C9—Co1—N2—C2	89.0 (4)	O4—N4—C4—C8	0.7 (8)
N6—Co1—N2—C2	−91.0 (4)	Co1—N4—C4—C8	−176.1 (4)
N1—Co1—N2—O2	178.7 (5)	N3—C3—C4—N4	−0.9 (7)
N3—Co1—N2—O2	−2.4 (5)	C7—C3—C4—N4	177.8 (5)
C9—Co1—N2—O2	−92.4 (5)	N3—C3—C4—C8	177.4 (5)
N6—Co1—N2—O2	87.6 (5)	C7—C3—C4—C8	−3.9 (9)
N2—Co1—N3—C3	−175.7 (4)	N2—Co1—C9—C10	−28.3 (5)
N4—Co1—N3—C3	1.6 (4)	N1—Co1—C9—C10	53.1 (5)
C9—Co1—N3—C3	−84.7 (4)	N4—Co1—C9—C10	151.8 (5)
N6—Co1—N3—C3	97.4 (5)	N3—Co1—C9—C10	−126.9 (5)
N2—Co1—N3—O3	3.5 (4)	Co1—C9—C10—C11	−177.4 (4)
N4—Co1—N3—O3	−179.2 (4)	C12—N5—C11—O5	−0.4 (10)
C9—Co1—N3—O3	94.6 (5)	C13—N5—C11—O5	−178.3 (7)
N6—Co1—N3—O3	−83.3 (4)	C12—N5—C11—C10	−179.1 (6)
N1—Co1—N4—C4	176.7 (4)	C13—N5—C11—C10	3.0 (10)
N3—Co1—N4—C4	−2.2 (4)	C9—C10—C11—O5	−100.0 (7)
C9—Co1—N4—C4	88.2 (4)	C9—C10—C11—N5	78.8 (7)
N6—Co1—N4—C4	−91.8 (4)	Co1—N6—C20—C21	91.0 (6)
N1—Co1—N4—O4	0.1 (4)	Co1—N6—C20—C27	−145.9 (6)
N3—Co1—N4—O4	−178.8 (4)	N6—C20—C21—C22	−135.3 (6)
C9—Co1—N4—O4	−88.4 (4)	C27—C20—C21—C22	101.7 (8)
N6—Co1—N4—O4	91.6 (4)	N6—C20—C21—C26	48.4 (7)
N2—Co1—N6—C20	−178.3 (5)	C27—C20—C21—C26	−74.7 (8)
N1—Co1—N6—C20	100.4 (5)	C26—C21—C22—C23	−0.6 (11)
N4—Co1—N6—C20	1.6 (5)	C20—C21—C22—C23	−177.2 (7)
N3—Co1—N6—C20	−79.6 (5)	C21—C22—C23—C24	0.6 (16)
O1—N1—C1—C2	−178.2 (4)	C22—C23—C24—C25	−1 (2)
Co1—N1—C1—C2	−1.2 (6)	C23—C24—C25—C26	1.3 (19)
O1—N1—C1—C5	−0.4 (8)	C22—C21—C26—C25	0.9 (10)
Co1—N1—C1—C5	176.6 (5)	C20—C21—C26—C25	177.4 (6)
O2—N2—C2—C1	−179.3 (5)	C24—C25—C26—C21	−1.3 (14)
Co1—N2—C2—C1	−0.7 (5)	C9—C10—C11—N5	78.8 (7)
O2—N2—C2—C6	1.3 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H01···O4	1.01	1.46	2.476 (6)	180
O3—H03···O2	1.00	1.47	2.475 (7)	180
N6—H06B···O5^i	0.90	2.17	2.919 (7)	141

Symmetry code: (i) −x, y−1/2, −z.