Direct observation of deuterium migration in crystalline-state reaction by single-crystal neutron diffraction. III. Photoracemization of 1-cyanoethyl cobaloxime complexes

The H atoms bonded to the chiral C atoms (stereogenic center) of the 1-cyanoethyl groups in two cobalt complexes, [(R)-1-cyanoethyl]bis(dimethylglyoximato)(pyridine)cobalt(III) (2) and [(R,S)-1-cyanoethyl]bis(dimethylglyoximato)(piperidine)cobalt(III) (3), were replaced with D atoms, such as Co-C*D(CH₃)CN. The crystals of the two cobalt complexes were irradiated with a xenon lamp for 72 h and 27 d, respectively. The unit-cell dimensions were gradually changed with retention of the single-crystal form. The crystal structures after irradiation were determined by neutron diffraction. In each crystal the chiral 1-cyanoethyl group of one of the two crystallographically independent molecules was partly inverted to the opposite configuration, whereas that of the other molecule kept the original configuration. The C*-D bond in the inverted group was completely conserved in the process of the inversion of the chiral alkyl group. This suggests that the inversion of the chiral 1-cyanoethyl group proceeds with the rotation of the cyanoethyl radical after the Co-C bond cleavage by photo-irradiation so that the opposite side of the radical faces the Co atom. This is followed by recombination of the Co-C bond to form the inverted 1-cyanoethyl group.

Computing details

Data collection: local program for 2-neutron, 3-neutron; SMART (Siemens, 1996) for 3-initial, 3-irradiated. Cell refinement: local program for 2-neutron, 3-neutron; SAINT (Siemens, 1994) for 3-initial, 3-irradiated. Data reduction: TEXSAN for 2-initial, 2-irradiated; local program for 2-neutron, 3-neutron; SAINT (Siemens, 1994) for 3-initial, 3-irradiated. Program(s) used to solve structure: SIR92 (Cascarano et al., 1994) for 2-initial, 2-irradiated, 3-initial, 3-irradiated; initial structure was determined by X-ray for 2-neutron, 3-neutron. Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for 2-initial, 2-irradiated, 3-initial, 3-irradiated, 3-neutron; SHELXL93 (Sheldrick, 1993) for 2-neutron. Molecular graphics: TEXSAN for 2-initial, 2-irradiated; ORTEPIII for 2-neutron, 3-initial, 3-irradiated, 3-neutron. Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) for 2-initial, 2-irradiated, 3-initial, 3-irradiated.

Figures

(2-initial) '[(R)-1-cyanoethyl](pyridine)bis(dimethylglyoximato)cobalt(III) initial'

Crystal data

C16H23CoN6O4	F(000) = 880
Mr = 422.33	Dx = 1.442 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 16.0665 (15) Å	Cell parameters from 25 reflections
b = 12.5929 (11) Å	θ = 14–15°
c = 9.6440 (11) Å	µ = 0.92 mm^−1
β = 94.626 (9)°	T = 293 K
V = 1944.9 (3) Å^3	Plate, red
Z = 4	0.3 × 0.3 × 0.2 mm

Data collection

Rigaku AFC7R diffractometer	3294 reflections with I > 2σ(I)
Radiation source: rotate anode	Rint = 0.030
Graphite monochromator	θmax = 27.5°, θmin = 2.5°
2θ–ω scans	h = −20→0
Absorption correction: ψ scans (North et al., 1968)	k = −16→0
Tmin = 0.637, Tmax = 0.832	l = −12→12
4690 measured reflections	3 standard reflections every 100 reflections
4542 independent reflections	intensity decay: 0.9%

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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.173	w = 1/[σ^2(Fo^2) + (0.1241P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
4542 reflections	Δρmax = 0.76 e Å^−3
498 parameters	Δρmin = −1.13 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (3)

Special details

Experimental. The crystal was obtained by slow evaporation from methanol/water.

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	0.02086 (6)	0.89730 (7)	0.73560 (9)	0.0326 (2)
O1	0.0502 (4)	0.9458 (6)	1.0236 (6)	0.0544 (16)
HO1	0.112 (9)	0.998 (8)	0.964 (9)	0.22 (11)*
O2	−0.1059 (5)	0.7670 (5)	0.6024 (7)	0.0494 (17)
O3	−0.0044 (4)	0.8458 (6)	0.4470 (5)	0.0495 (15)
HO3	−0.035 (5)	0.815 (5)	0.478 (5)	0.074*
O4	0.1436 (4)	1.0357 (6)	0.8665 (7)	0.0517 (17)
N1	0.0040 (4)	0.8917 (8)	0.9262 (6)	0.0414 (14)
N2	−0.0732 (4)	0.8078 (6)	0.7244 (7)	0.0388 (15)
N3	0.0404 (4)	0.9029 (7)	0.5456 (6)	0.0382 (14)
N4	0.1136 (4)	0.9932 (5)	0.7481 (7)	0.0364 (15)
N5	−0.0591 (4)	1.0237 (5)	0.7090 (7)	0.0365 (15)
N6	0.2139 (6)	0.7940 (8)	0.9540 (10)	0.068 (2)
C1	−0.0622 (5)	0.8408 (8)	0.9594 (9)	0.045 (2)
C2	−0.1058 (5)	0.7886 (7)	0.8412 (9)	0.0424 (19)
C3	0.0987 (5)	0.9638 (7)	0.5107 (9)	0.0438 (18)
C4	0.1417 (5)	1.0192 (6)	0.6309 (9)	0.0410 (17)
C5	−0.0889 (7)	0.8368 (10)	1.1030 (9)	0.063 (3)
H5A	−0.0435	0.8586	1.1676	0.095*
H5B	−0.1050	0.7656	1.1241	0.095*
H5C	−0.1355	0.8836	1.1103	0.095*
C6	−0.1807 (5)	0.7202 (9)	0.8502 (10)	0.056 (2)
H6A	−0.2023	0.7000	0.7583	0.084*
H6B	−0.2226	0.7587	0.8950	0.084*
H6C	−0.1654	0.6576	0.9033	0.084*
C7	0.1225 (6)	0.9798 (8)	0.3665 (9)	0.055 (2)
H7A	0.0982	0.9247	0.3075	0.082*
H7B	0.1822	0.9773	0.3660	0.082*
H7C	0.1026	1.0476	0.3327	0.082*
C8	0.2106 (5)	1.0961 (8)	0.6221 (12)	0.063 (3)
H8A	0.2373	1.1083	0.7133	0.095*
H8B	0.1887	1.1619	0.5843	0.095*
H8C	0.2505	1.0681	0.5628	0.095*
C9	−0.0589 (7)	1.1021 (8)	0.8030 (9)	0.057 (2)
H9	−0.0212	1.0998	0.8814	0.09 (4)*
C10	−0.1136 (9)	1.1859 (10)	0.7854 (12)	0.081 (4)
H10	−0.1136	1.2385	0.8530	0.11 (4)*
C11	−0.1673 (7)	1.1923 (9)	0.6708 (11)	0.065 (3)
H11	−0.2037	1.2494	0.6587	0.04 (2)*
C12	−0.1675 (6)	1.1147 (8)	0.5737 (10)	0.057 (2)
H12	−0.2041	1.1167	0.4939	0.028 (17)*
C13	−0.1115 (6)	1.0327 (7)	0.5978 (10)	0.045 (2)
H13	−0.1106	0.9799	0.5306	0.06 (3)*
C14	0.1005 (6)	0.7714 (8)	0.7499 (11)	0.048 (2)
H14	0.1297	0.7726	0.6645	0.058*
C15	0.1660 (6)	0.7845 (8)	0.8655 (10)	0.045 (2)
C16	0.0640 (6)	0.6606 (7)	0.7586 (12)	0.064 (3)
H16A	0.0146	0.6552	0.6961	0.096*
H16B	0.0501	0.6473	0.8520	0.096*
H16C	0.1043	0.6093	0.7334	0.096*
Co2	0.49339 (6)	0.72614 (7)	0.74480 (9)	0.0334 (2)
O5	0.4643 (4)	0.6789 (6)	0.4575 (6)	0.0524 (15)
H5	0.432 (4)	0.626 (7)	0.500 (5)	0.079*
O6	0.6197 (4)	0.8562 (5)	0.8783 (7)	0.0480 (16)
O7	0.5227 (4)	0.7710 (6)	1.0364 (6)	0.0555 (17)
HO7	0.562 (10)	0.805 (9)	0.999 (10)	0.23 (12)*
O8	0.3660 (5)	0.5931 (6)	0.6120 (7)	0.0500 (16)
N7	0.5131 (4)	0.7302 (8)	0.5573 (6)	0.0432 (15)
N8	0.5879 (4)	0.8169 (6)	0.7587 (7)	0.0382 (15)
N9	0.4728 (4)	0.7191 (7)	0.9347 (6)	0.0408 (14)
N10	0.3984 (4)	0.6363 (6)	0.7334 (7)	0.0416 (16)
N11	0.5686 (5)	0.5954 (6)	0.7698 (7)	0.0397 (16)
C17	0.5760 (6)	0.7832 (7)	0.5211 (9)	0.0451 (19)
C18	0.6208 (5)	0.8354 (7)	0.6407 (9)	0.0451 (19)
C19	0.4139 (5)	0.6596 (7)	0.9705 (8)	0.0411 (17)
C20	0.3698 (5)	0.6094 (7)	0.8505 (9)	0.0419 (18)
C21	0.6036 (7)	0.7898 (10)	0.3780 (10)	0.068 (3)
H21A	0.5866	0.7269	0.3272	0.103*
H21B	0.6633	0.7960	0.3826	0.103*
H21C	0.5788	0.8509	0.3317	0.103*
C22	0.6945 (6)	0.9049 (9)	0.6304 (11)	0.063 (3)
H22A	0.6778	0.9779	0.6351	0.094*
H22B	0.7181	0.8922	0.5436	0.094*
H22C	0.7354	0.8897	0.7059	0.094*
C23	0.3942 (7)	0.6420 (9)	1.1157 (9)	0.059 (3)
H23A	0.4362	0.6748	1.1779	0.089*
H23B	0.3928	0.5671	1.1341	0.089*
H23C	0.3407	0.6725	1.1294	0.089*
C24	0.2988 (7)	0.5334 (8)	0.8602 (12)	0.066 (3)
H24A	0.2630	0.5358	0.7756	0.099*
H24B	0.2676	0.5528	0.9371	0.099*
H24C	0.3204	0.4627	0.8741	0.099*
C25	0.5589 (6)	0.5118 (8)	0.6847 (9)	0.049 (2)
H25	0.5166	0.5140	0.6129	0.059*
C26	0.6083 (6)	0.4226 (7)	0.6983 (10)	0.056 (2)
H26	0.5979	0.3646	0.6397	0.067*
C27	0.6742 (6)	0.4205 (7)	0.8013 (10)	0.052 (2)
H27	0.7098	0.3623	0.8107	0.062*
C28	0.6855 (5)	0.5072 (7)	0.8894 (9)	0.051 (2)
H28	0.7283	0.5072	0.9604	0.061*
C29	0.6335 (6)	0.5920 (8)	0.8712 (10)	0.044 (2)
H29	0.6424	0.6503	0.9298	0.053*
C30	0.4245 (5)	0.8617 (7)	0.7111 (9)	0.0435 (18)
H30	0.4554	0.9063	0.6498	0.052*
C31	0.3453 (6)	0.8392 (8)	0.6359 (10)	0.043 (2)
C32	0.4114 (7)	0.9286 (8)	0.8381 (12)	0.068 (3)
H32A	0.4643	0.9544	0.8777	0.102*
H32B	0.3857	0.8861	0.9056	0.102*
H32C	0.3758	0.9876	0.8116	0.102*
N12	0.2812 (6)	0.8252 (8)	0.5742 (10)	0.068 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0352 (5)	0.0324 (5)	0.0292 (4)	−0.0029 (4)	−0.0027 (4)	−0.0021 (4)
O1	0.067 (4)	0.059 (4)	0.035 (3)	−0.004 (3)	−0.008 (3)	−0.009 (3)
O2	0.057 (4)	0.046 (4)	0.045 (3)	−0.017 (3)	0.001 (3)	−0.011 (3)
O3	0.053 (3)	0.062 (4)	0.033 (2)	−0.011 (3)	−0.001 (2)	−0.014 (2)
O4	0.047 (4)	0.053 (4)	0.052 (3)	−0.014 (3)	−0.019 (3)	0.000 (3)
N1	0.046 (3)	0.043 (4)	0.034 (3)	0.002 (4)	−0.004 (3)	−0.005 (4)
N2	0.042 (3)	0.035 (4)	0.039 (3)	0.003 (3)	0.000 (3)	−0.002 (3)
N3	0.039 (3)	0.037 (4)	0.037 (3)	0.002 (4)	−0.002 (2)	0.001 (4)
N4	0.037 (3)	0.029 (3)	0.040 (3)	−0.009 (3)	−0.012 (3)	−0.002 (3)
N5	0.042 (3)	0.034 (4)	0.034 (3)	−0.001 (3)	0.005 (3)	0.000 (3)
N6	0.062 (5)	0.065 (6)	0.074 (5)	0.001 (4)	−0.015 (5)	0.003 (5)
C1	0.047 (4)	0.048 (5)	0.041 (4)	0.007 (4)	0.006 (4)	0.009 (4)
C2	0.046 (4)	0.038 (4)	0.044 (4)	0.001 (3)	0.008 (4)	0.008 (4)
C3	0.049 (4)	0.040 (4)	0.043 (4)	0.005 (4)	0.008 (4)	0.005 (3)
C4	0.036 (4)	0.030 (4)	0.055 (4)	0.001 (3)	−0.003 (3)	0.005 (3)
C5	0.078 (7)	0.073 (7)	0.040 (4)	0.001 (6)	0.013 (5)	0.003 (4)
C6	0.049 (4)	0.057 (5)	0.064 (5)	−0.004 (5)	0.011 (4)	0.010 (5)
C7	0.060 (5)	0.057 (6)	0.048 (5)	0.006 (5)	0.007 (4)	0.010 (4)
C8	0.041 (4)	0.057 (6)	0.088 (7)	−0.009 (4)	−0.011 (4)	0.024 (5)
C9	0.072 (6)	0.056 (6)	0.042 (4)	0.010 (5)	−0.007 (4)	−0.011 (4)
C10	0.126 (11)	0.061 (7)	0.058 (6)	0.027 (7)	0.009 (7)	−0.014 (5)
C11	0.065 (6)	0.054 (6)	0.076 (6)	0.019 (5)	0.009 (5)	0.000 (5)
C12	0.056 (5)	0.055 (5)	0.059 (5)	0.000 (4)	0.000 (4)	0.007 (4)
C13	0.046 (5)	0.039 (5)	0.047 (5)	−0.001 (4)	−0.013 (4)	−0.005 (4)
C14	0.051 (5)	0.042 (5)	0.051 (5)	−0.001 (4)	0.001 (4)	−0.002 (4)
C15	0.039 (4)	0.040 (5)	0.055 (5)	−0.004 (3)	−0.004 (4)	0.001 (4)
C16	0.053 (5)	0.034 (4)	0.102 (8)	−0.001 (4)	−0.013 (5)	0.001 (5)
Co2	0.0361 (5)	0.0320 (5)	0.0312 (4)	−0.0025 (4)	−0.0031 (4)	−0.0012 (4)
O5	0.063 (4)	0.059 (4)	0.032 (3)	−0.005 (3)	−0.009 (3)	0.000 (3)
O6	0.044 (3)	0.049 (4)	0.050 (3)	−0.012 (3)	−0.012 (3)	−0.003 (3)
O7	0.064 (4)	0.063 (4)	0.039 (3)	−0.012 (3)	−0.002 (3)	−0.012 (3)
O8	0.058 (4)	0.045 (4)	0.044 (3)	−0.010 (3)	−0.012 (3)	−0.012 (3)
N7	0.050 (4)	0.039 (4)	0.039 (3)	−0.002 (4)	−0.003 (3)	0.002 (4)
N8	0.040 (3)	0.031 (4)	0.043 (3)	−0.003 (3)	−0.004 (3)	−0.001 (3)
N9	0.047 (3)	0.036 (4)	0.039 (3)	0.002 (4)	−0.003 (3)	−0.009 (4)
N10	0.040 (3)	0.039 (4)	0.044 (3)	0.008 (3)	−0.001 (3)	0.000 (3)
N11	0.048 (4)	0.036 (4)	0.035 (3)	−0.003 (3)	0.002 (3)	0.001 (3)
C17	0.050 (5)	0.043 (5)	0.041 (4)	0.004 (4)	0.000 (4)	0.012 (4)
C18	0.042 (4)	0.038 (5)	0.055 (5)	0.000 (3)	0.003 (4)	0.011 (4)
C19	0.042 (4)	0.040 (5)	0.041 (4)	0.002 (3)	0.001 (3)	0.000 (3)
C20	0.041 (4)	0.036 (4)	0.048 (4)	0.004 (3)	0.001 (4)	0.004 (4)
C21	0.067 (6)	0.094 (9)	0.047 (5)	0.011 (6)	0.013 (5)	0.016 (5)
C22	0.052 (5)	0.054 (6)	0.081 (6)	−0.008 (5)	0.002 (5)	0.021 (6)
C23	0.069 (6)	0.062 (6)	0.048 (5)	0.004 (5)	0.015 (5)	0.009 (5)
C24	0.064 (6)	0.045 (5)	0.092 (7)	−0.016 (5)	0.020 (6)	0.001 (5)
C25	0.055 (5)	0.047 (5)	0.043 (4)	0.007 (4)	−0.007 (4)	−0.004 (4)
C26	0.068 (6)	0.043 (5)	0.057 (5)	0.015 (4)	0.000 (4)	−0.011 (4)
C27	0.055 (5)	0.038 (5)	0.063 (5)	0.011 (3)	0.012 (4)	0.011 (4)
C28	0.037 (4)	0.052 (5)	0.062 (5)	−0.001 (4)	−0.009 (4)	0.017 (4)
C29	0.046 (5)	0.040 (5)	0.046 (4)	−0.006 (4)	−0.004 (4)	0.005 (4)
C30	0.042 (4)	0.037 (4)	0.051 (4)	0.006 (3)	−0.005 (3)	0.000 (3)
C31	0.046 (5)	0.042 (5)	0.042 (4)	0.009 (4)	0.002 (4)	0.004 (4)
C32	0.073 (7)	0.048 (5)	0.081 (7)	0.022 (5)	−0.005 (5)	−0.022 (5)
N12	0.059 (5)	0.062 (5)	0.081 (6)	0.007 (4)	−0.013 (4)	0.001 (5)

Geometric parameters (Å, º)

Co1—N1	1.881 (6)	Co2—N7	1.862 (6)
Co1—N2	1.881 (7)	Co2—N9	1.889 (6)
Co1—N3	1.885 (6)	Co2—N10	1.896 (8)
Co1—N4	1.914 (7)	Co2—N8	1.896 (7)
Co1—C14	2.035 (10)	Co2—N11	2.045 (8)
Co1—N5	2.048 (7)	Co2—C30	2.047 (8)
O1—N1	1.336 (9)	O5—N7	1.355 (9)
O2—N2	1.351 (10)	O6—N8	1.320 (10)
O3—N3	1.353 (9)	O7—N9	1.381 (9)
O4—N4	1.317 (9)	O8—N10	1.356 (10)
N1—C1	1.303 (12)	N7—C17	1.282 (12)
N2—C2	1.303 (10)	N8—C18	1.314 (11)
N3—C3	1.276 (11)	N9—C19	1.276 (11)
N4—C4	1.292 (11)	N10—C20	1.298 (10)
N5—C13	1.313 (12)	N11—C25	1.336 (12)
N5—C9	1.340 (11)	N11—C29	1.372 (12)
N6—C15	1.109 (13)	C17—C18	1.465 (13)
C1—C2	1.447 (13)	C17—C21	1.486 (12)
C1—C5	1.484 (11)	C18—C22	1.482 (12)
C2—C6	1.489 (12)	C19—C20	1.453 (12)
C3—C4	1.476 (12)	C19—C23	1.477 (11)
C3—C7	1.486 (11)	C20—C24	1.497 (12)
C4—C8	1.479 (11)	C25—C26	1.377 (13)
C9—C10	1.376 (15)	C26—C27	1.391 (14)
C10—C11	1.348 (16)	C27—C28	1.386 (13)
C11—C12	1.353 (14)	C28—C29	1.359 (13)
C12—C13	1.378 (14)	C30—C31	1.441 (14)
C14—C15	1.479 (14)	C30—C32	1.515 (12)
C14—C16	1.519 (13)	C31—N12	1.159 (14)
N1—Co1—N2	81.7 (3)	N7—Co2—N9	178.8 (5)
N1—Co1—N3	178.7 (3)	N7—Co2—N10	99.2 (3)
N2—Co1—N3	99.4 (3)	N9—Co2—N10	79.9 (3)
N1—Co1—N4	97.8 (3)	N7—Co2—N8	81.6 (3)
N2—Co1—N4	177.6 (3)	N9—Co2—N8	99.3 (3)
N3—Co1—N4	81.2 (3)	N10—Co2—N8	179.2 (3)
N1—Co1—C14	92.5 (4)	N7—Co2—N11	89.5 (3)
N2—Co1—C14	92.0 (4)	N9—Co2—N11	89.8 (3)
N3—Co1—C14	86.7 (4)	N10—Co2—N11	89.5 (3)
N4—Co1—C14	90.3 (3)	N8—Co2—N11	90.8 (3)
N1—Co1—N5	90.8 (3)	N7—Co2—C30	87.4 (4)
N2—Co1—N5	88.0 (3)	N9—Co2—C30	93.4 (4)
N3—Co1—N5	90.1 (3)	N10—Co2—C30	93.8 (4)
N4—Co1—N5	89.7 (3)	N8—Co2—C30	85.9 (3)
C14—Co1—N5	176.7 (4)	N11—Co2—C30	175.8 (3)
C1—N1—O1	119.7 (6)	C17—N7—O5	118.6 (7)
C1—N1—Co1	116.3 (6)	C17—N7—Co2	118.5 (7)
O1—N1—Co1	123.5 (6)	O5—N7—Co2	122.9 (5)
C2—N2—O2	121.8 (7)	C18—N8—O6	122.4 (7)
C2—N2—Co1	116.0 (6)	C18—N8—Co2	114.9 (6)
O2—N2—Co1	122.2 (5)	O6—N8—Co2	122.6 (5)
C3—N3—O3	119.6 (6)	C19—N9—O7	119.1 (6)
C3—N3—Co1	117.5 (6)	C19—N9—Co2	118.8 (6)
O3—N3—Co1	122.8 (5)	O7—N9—Co2	122.0 (5)
C4—N4—O4	121.7 (7)	C20—N10—O8	120.5 (7)
C4—N4—Co1	115.5 (6)	C20—N10—Co2	116.4 (6)
O4—N4—Co1	122.7 (5)	O8—N10—Co2	122.7 (5)
C13—N5—C9	117.1 (8)	C25—N11—C29	117.3 (8)
C13—N5—Co1	121.6 (6)	C25—N11—Co2	121.5 (6)
C9—N5—Co1	121.4 (6)	C29—N11—Co2	121.1 (6)
N1—C1—C2	112.5 (7)	N7—C17—C18	111.6 (7)
N1—C1—C5	123.3 (9)	N7—C17—C21	125.6 (9)
C2—C1—C5	124.1 (8)	C18—C17—C21	122.7 (8)
N2—C2—C1	113.2 (7)	N8—C18—C17	113.3 (7)
N2—C2—C6	122.8 (8)	N8—C18—C22	122.8 (9)
C1—C2—C6	124.0 (7)	C17—C18—C22	123.9 (8)
N3—C3—C4	112.6 (7)	N9—C19—C20	111.4 (7)
N3—C3—C7	125.3 (9)	N9—C19—C23	124.5 (8)
C4—C3—C7	122.1 (8)	C20—C19—C23	124.1 (8)
N4—C4—C3	113.1 (7)	N10—C20—C19	113.2 (7)
N4—C4—C8	122.2 (8)	N10—C20—C24	123.1 (9)
C3—C4—C8	124.7 (8)	C19—C20—C24	123.7 (8)
N5—C9—C10	121.0 (10)	N11—C25—C26	123.1 (9)
C11—C10—C9	120.5 (10)	C25—C26—C27	118.9 (9)
C10—C11—C12	119.4 (10)	C28—C27—C26	118.5 (8)
C11—C12—C13	117.3 (10)	C29—C28—C27	119.4 (9)
N5—C13—C12	124.7 (9)	C28—C29—N11	122.7 (9)
C15—C14—C16	108.3 (8)	C31—C30—C32	110.0 (8)
C15—C14—Co1	111.7 (7)	C31—C30—Co2	111.1 (6)
C16—C14—Co1	118.4 (7)	C32—C30—Co2	116.4 (6)
N6—C15—C14	178.6 (10)	N12—C31—C30	177.4 (11)

(2-irradiated) '[(R)-1-cyanoethyl](pyridine)bis(dimethylglyoximato)cobalt(III) irradiated'

Crystal data

C16H23CoN6O4	F(000) = 880
Mr = 422.33	Dx = 1.444 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 16.023 (5) Å	Cell parameters from 25 reflections
b = 12.6272 (18) Å	θ = 14–15°
c = 9.628 (2) Å	µ = 0.92 mm^−1
β = 94.23 (2)°	T = 293 K
V = 1942.6 (7) Å^3	Plate, red
Z = 4	0.2 × 0.2 × 0.1 mm

Data collection

Rigaku AFC7R diffractometer	4898 reflections with I > 2σ(I)
Radiation source: rotate anode	Rint = 0.064
Graphite monochromator	θmax = 37.5°, θmin = 2.6°
2θ–ω scans	h = −21→21
Absorption correction: ψ scans (North et al., 1968)	k = 0→16
Tmin = 0.731, Tmax = 0.832	l = −13→0
8931 measured reflections	3 standard reflections every 100 reflections
8580 independent reflections	intensity decay: 1.0%

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.155	Calculated w = 1/[σ^2(Fo^2) + (0.0888P)^2 + 0.059P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.012
8580 reflections	Δρmax = 1.02 e Å^−3
587 parameters	Δρmin = −0.53 e Å^−3
16 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (2)

Special details

Experimental. The crystal was obtained by slow evaporation from methanol/water.

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	0.020095 (12)	0.897191 (15)	0.735478 (18)	0.03135 (4)
O1	0.04912 (8)	0.94416 (12)	1.02461 (11)	0.0551 (4)
HO1	0.1079 (11)	0.9943 (16)	0.9663 (19)	0.049 (5)*
O2	−0.10674 (7)	0.76742 (10)	0.60443 (12)	0.0444 (3)
O3	−0.00565 (8)	0.84631 (11)	0.44582 (11)	0.0481 (3)
HO3	−0.0407	0.8108	0.4828	0.072*
O4	0.14360 (8)	1.03611 (10)	0.86621 (13)	0.0523 (3)
N1	0.00235 (8)	0.89142 (12)	0.92708 (11)	0.0375 (3)
N2	−0.07476 (8)	0.80787 (11)	0.72431 (14)	0.0390 (3)
N3	0.03911 (7)	0.90304 (12)	0.54370 (11)	0.0365 (3)
N4	0.11208 (8)	0.99236 (11)	0.74656 (14)	0.0383 (3)
N5	−0.05881 (8)	1.02293 (10)	0.71014 (12)	0.0347 (3)
N6	0.21542 (11)	0.79322 (16)	0.9501 (2)	0.0659 (6)
C1	−0.06293 (12)	0.83971 (15)	0.96148 (16)	0.0454 (4)
C2	−0.10854 (9)	0.78872 (13)	0.84168 (17)	0.0384 (4)
C3	0.09867 (9)	0.96445 (14)	0.50894 (16)	0.0386 (4)
C4	0.14152 (10)	1.01854 (13)	0.62980 (17)	0.0408 (4)
C5	−0.09226 (14)	0.8347 (2)	1.10548 (19)	0.0636 (6)
H5A	−0.0477	0.8563	1.1716	0.095*
H5B	−0.1086	0.7635	1.1254	0.095*
H5C	−0.1393	0.8812	1.1117	0.095*
C6	−0.18373 (11)	0.72152 (18)	0.8547 (2)	0.0552 (5)
H6A	−0.2063	0.7006	0.7636	0.083*
H6B	−0.2251	0.7609	0.9002	0.083*
H6C	−0.1684	0.6596	0.9086	0.083*
C7	0.12227 (12)	0.98043 (17)	0.36260 (19)	0.0543 (5)
H7A	0.0960 (10)	0.9221 (9)	0.3051 (15)	0.081*
H7B	0.1864 (14)	0.993 (2)	0.354 (2)	0.081*
H7C	0.1208 (14)	1.057 (2)	0.355 (2)	0.081*
C8	0.21118 (11)	1.09581 (16)	0.6169 (2)	0.0555 (5)
H8A	0.2313 (14)	1.101 (2)	0.709 (2)	0.083*
H8B	0.1982 (14)	1.159 (2)	0.575 (2)	0.083*
H8C	0.2628 (6)	1.0690 (15)	0.5806 (17)	0.083*
C9	−0.05792 (14)	1.10352 (16)	0.80230 (18)	0.0568 (5)
H9	−0.0156 (11)	1.0996 (15)	0.8844 (18)	0.044 (5)*
C10	−0.11286 (16)	1.1879 (2)	0.7875 (2)	0.0753 (7)
H10	−0.1163 (11)	1.2459 (16)	0.8515 (18)	0.045 (5)*
C11	−0.16734 (13)	1.19537 (17)	0.6723 (2)	0.0618 (6)
H11	−0.1956 (8)	1.2612 (7)	0.6438 (17)	0.049 (5)*
C12	−0.16883 (11)	1.11544 (16)	0.5755 (2)	0.0531 (5)
H12	−0.2041 (10)	1.1230 (16)	0.4986 (18)	0.042 (5)*
C13	−0.11462 (10)	1.03116 (14)	0.59738 (18)	0.0429 (4)
H13	−0.1160 (10)	0.9670 (14)	0.5303 (16)	0.032 (4)*
C14	0.10139 (10)	0.76995 (15)	0.74920 (19)	0.0456 (4)
H14	0.1177 (12)	0.7875 (17)	0.650 (2)	0.055*
C15	0.16449 (11)	0.78613 (14)	0.86167 (19)	0.0460 (4)
C16	0.06512 (13)	0.66158 (15)	0.7550 (2)	0.0605 (6)
H16A	0.0159	0.6572	0.6921	0.091*
H16B	0.0506	0.6470	0.8481	0.091*
H16C	0.1055	0.6106	0.7286	0.091*
Co2	0.490260 (12)	0.726250 (16)	0.748951 (19)	0.03552 (5)
O5	0.46003 (9)	0.67731 (13)	0.46009 (12)	0.0586 (4)
H5	0.4333	0.6322	0.4990	0.088*
O6	0.61721 (8)	0.85569 (10)	0.88189 (14)	0.0512 (4)
O7	0.51915 (9)	0.77131 (12)	1.04213 (13)	0.0551 (4)
HO7	0.5542 (12)	0.8003 (17)	0.990 (2)	0.058 (6)*
O8	0.36387 (8)	0.59337 (10)	0.61794 (13)	0.0515 (3)
N7	0.50952 (10)	0.73159 (14)	0.55716 (13)	0.0481 (4)
N8	0.58435 (8)	0.81598 (11)	0.76158 (14)	0.0392 (3)
N9	0.47036 (8)	0.71865 (12)	0.94040 (13)	0.0424 (4)
N10	0.39546 (8)	0.63539 (11)	0.73871 (14)	0.0409 (3)
N11	0.56729 (8)	0.59644 (11)	0.77385 (13)	0.0362 (3)
C17	0.57412 (12)	0.78363 (15)	0.52403 (19)	0.0480 (5)
C18	0.61847 (11)	0.83513 (15)	0.6440 (2)	0.0474 (5)
C19	0.41102 (11)	0.66046 (14)	0.97679 (18)	0.0444 (4)
C20	0.36631 (10)	0.60741 (14)	0.85581 (19)	0.0433 (4)
C21	0.60136 (16)	0.7889 (2)	0.3792 (2)	0.0695 (7)
H21A	0.5840	0.7257	0.3296	0.104*
H21B	0.6612	0.7949	0.3824	0.104*
H21C	0.5764	0.8495	0.3324	0.104*
C22	0.69333 (12)	0.90470 (18)	0.6335 (2)	0.0634 (6)
H22A	0.6801 (13)	0.9827 (7)	0.638 (3)	0.095*
H22B	0.6837 (15)	0.933 (2)	0.534 (2)	0.095*
H22C	0.7386 (15)	0.863 (2)	0.635 (3)	0.095*
C23	0.38819 (14)	0.64097 (18)	1.1204 (2)	0.0601 (6)
H23A	0.4291	0.6729	1.1852	0.090*
H23B	0.3864	0.5661	1.1371	0.090*
H23C	0.3342	0.6712	1.1324	0.090*
C24	0.29626 (12)	0.53290 (18)	0.8666 (2)	0.0601 (6)
H24A	0.2604	0.5351	0.7822	0.090*
H24B	0.2650	0.5526	0.9438	0.090*
H24C	0.3178	0.4625	0.8807	0.090*
C25	0.56003 (12)	0.51356 (17)	0.68795 (19)	0.0505 (5)
H25	0.5197	0.5167	0.6134	0.061*
C26	0.60757 (14)	0.42530 (17)	0.7025 (2)	0.0588 (6)
H26	0.5973	0.3674	0.6441	0.071*
C27	0.67195 (12)	0.42338 (16)	0.8066 (2)	0.0543 (5)
H27	0.7077	0.3654	0.8172	0.065*
C28	0.68173 (12)	0.50894 (16)	0.8935 (2)	0.0541 (5)
H28	0.7243	0.5097	0.9647	0.065*
C29	0.62826 (10)	0.59375 (15)	0.87488 (18)	0.0458 (4)
H29	0.6350	0.6512	0.9351	0.055*
C30A	0.42522 (2)	0.86270 (5)	0.70806 (5)	0.0420 (6)	0.707 (2)
H30A	0.4572	0.9063	0.6467	0.050*	0.707 (2)
C31A	0.34464 (2)	0.83926 (6)	0.63521 (5)	0.0478 (7)	0.707 (2)
C32A	0.41009 (7)	0.92778 (5)	0.83661 (5)	0.0643 (9)	0.707 (2)
H32A	0.4625	0.9542	0.8774	0.096*	0.707 (2)
H32B	0.3843	0.8841	0.9029	0.096*	0.707 (2)
H32C	0.3739	0.9862	0.8107	0.096*	0.707 (2)
N12A	0.28094 (2)	0.82303 (13)	0.57522 (9)	0.0628 (8)	0.707 (2)
C30B	0.40344 (3)	0.84768 (4)	0.75694 (5)	0.0376 (12)	0.293 (2)
H30B	0.3763	0.8401	0.8443	0.045*	0.293 (2)
C31B	0.33895 (2)	0.83800 (6)	0.64334 (5)	0.0417 (13)*	0.293 (2)
C32B	0.43961 (4)	0.95887 (3)	0.75381 (13)	0.065 (2)	0.293 (2)
H32D	0.4750	0.9710	0.8372	0.098*	0.293 (2)
H32E	0.3949	1.0096	0.7482	0.098*	0.293 (2)
H32F	0.4718	0.9662	0.6741	0.098*	0.293 (2)
N12B	0.28786 (3)	0.8302 (3)	0.55305 (6)	0.0548 (16)	0.293 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.03335 (7)	0.03069 (8)	0.02910 (6)	−0.00290 (8)	−0.00385 (6)	−0.00124 (7)
O1	0.0700 (8)	0.0619 (8)	0.0310 (5)	−0.0006 (7)	−0.0125 (5)	−0.0064 (5)
O2	0.0366 (5)	0.0519 (6)	0.0432 (5)	−0.0119 (5)	−0.0061 (4)	−0.0091 (5)
O3	0.0520 (6)	0.0560 (7)	0.0354 (5)	−0.0103 (6)	−0.0034 (5)	−0.0105 (5)
O4	0.0592 (7)	0.0447 (6)	0.0497 (6)	−0.0126 (5)	−0.0181 (5)	−0.0076 (5)
N1	0.0452 (6)	0.0383 (6)	0.0282 (4)	0.0019 (6)	−0.0038 (4)	0.0042 (5)
N2	0.0398 (6)	0.0372 (6)	0.0393 (6)	−0.0030 (5)	−0.0027 (5)	−0.0040 (5)
N3	0.0410 (5)	0.0373 (6)	0.0308 (5)	−0.0016 (6)	−0.0004 (4)	−0.0064 (5)
N4	0.0346 (5)	0.0375 (6)	0.0414 (6)	−0.0070 (5)	−0.0061 (5)	−0.0027 (5)
N5	0.0400 (6)	0.0330 (6)	0.0305 (5)	0.0010 (5)	−0.0005 (4)	−0.0031 (4)
N6	0.0524 (8)	0.0691 (11)	0.0725 (10)	0.0025 (9)	−0.0210 (8)	0.0064 (9)
C1	0.0586 (9)	0.0442 (8)	0.0337 (7)	0.0073 (7)	0.0060 (7)	0.0032 (6)
C2	0.0318 (6)	0.0353 (7)	0.0484 (8)	−0.0007 (5)	0.0051 (6)	0.0061 (6)
C3	0.0346 (6)	0.0408 (8)	0.0409 (7)	0.0017 (6)	0.0062 (6)	0.0039 (6)
C4	0.0366 (7)	0.0350 (7)	0.0494 (8)	−0.0011 (6)	−0.0053 (6)	0.0107 (6)
C5	0.0694 (11)	0.0783 (14)	0.0453 (9)	−0.0013 (12)	0.0182 (8)	0.0045 (10)
C6	0.0444 (8)	0.0552 (10)	0.0671 (10)	−0.0069 (9)	0.0116 (7)	0.0112 (9)
C7	0.0597 (10)	0.0577 (11)	0.0481 (8)	0.0029 (9)	0.0218 (7)	0.0105 (8)
C8	0.0420 (8)	0.0483 (9)	0.0759 (12)	−0.0156 (7)	0.0014 (8)	0.0119 (9)
C9	0.0806 (12)	0.0486 (9)	0.0394 (8)	0.0229 (9)	−0.0082 (8)	−0.0090 (7)
C10	0.0990 (15)	0.0651 (12)	0.0603 (11)	0.0323 (12)	−0.0036 (11)	−0.0152 (10)
C11	0.0643 (10)	0.0509 (10)	0.0701 (12)	0.0237 (8)	0.0035 (9)	0.0070 (9)
C12	0.0445 (8)	0.0517 (10)	0.0617 (10)	0.0041 (8)	−0.0056 (8)	0.0126 (8)
C13	0.0426 (7)	0.0377 (8)	0.0466 (8)	0.0030 (6)	−0.0093 (6)	−0.0015 (6)
C14	0.0365 (7)	0.0433 (8)	0.0554 (9)	0.0066 (6)	−0.0070 (7)	−0.0011 (7)
C15	0.0417 (7)	0.0415 (8)	0.0534 (9)	−0.0004 (7)	−0.0067 (7)	0.0078 (7)
C16	0.0552 (10)	0.0302 (8)	0.0943 (15)	0.0020 (7)	−0.0072 (10)	−0.0048 (9)
Co2	0.03865 (9)	0.02959 (8)	0.03644 (8)	−0.00111 (8)	−0.00988 (7)	−0.00229 (8)
O5	0.0739 (8)	0.0610 (8)	0.0383 (6)	−0.0157 (7)	−0.0138 (6)	−0.0029 (6)
O6	0.0545 (6)	0.0408 (6)	0.0558 (7)	−0.0116 (5)	−0.0129 (6)	−0.0083 (5)
O7	0.0630 (7)	0.0609 (8)	0.0397 (6)	−0.0149 (6)	−0.0083 (5)	−0.0138 (5)
O8	0.0553 (6)	0.0424 (6)	0.0527 (6)	−0.0099 (5)	−0.0243 (5)	−0.0043 (5)
N7	0.0661 (8)	0.0429 (7)	0.0333 (5)	−0.0066 (8)	−0.0102 (6)	0.0019 (6)
N8	0.0376 (6)	0.0319 (6)	0.0460 (6)	−0.0032 (5)	−0.0118 (5)	0.0011 (5)
N9	0.0449 (6)	0.0397 (7)	0.0410 (6)	0.0036 (6)	−0.0085 (5)	−0.0063 (6)
N10	0.0363 (6)	0.0346 (6)	0.0492 (6)	0.0005 (5)	−0.0147 (5)	−0.0050 (5)
N11	0.0338 (5)	0.0343 (6)	0.0397 (6)	−0.0008 (5)	−0.0025 (5)	0.0032 (5)
C17	0.0526 (9)	0.0448 (9)	0.0456 (8)	0.0048 (7)	−0.0037 (7)	0.0118 (7)
C18	0.0459 (8)	0.0390 (8)	0.0562 (9)	−0.0008 (7)	−0.0028 (7)	0.0097 (7)
C19	0.0493 (8)	0.0358 (8)	0.0477 (8)	0.0032 (7)	0.0019 (7)	0.0016 (7)
C20	0.0353 (7)	0.0344 (7)	0.0598 (9)	−0.0021 (6)	0.0009 (7)	−0.0066 (7)
C21	0.0908 (15)	0.0729 (14)	0.0451 (9)	0.0125 (13)	0.0079 (10)	0.0149 (9)
C22	0.0511 (9)	0.0506 (10)	0.0875 (13)	−0.0072 (9)	−0.0012 (9)	0.0203 (11)
C23	0.0782 (13)	0.0518 (11)	0.0518 (9)	−0.0027 (10)	0.0155 (9)	−0.0014 (9)
C24	0.0485 (9)	0.0494 (10)	0.0815 (13)	−0.0092 (8)	−0.0014 (10)	0.0108 (10)
C25	0.0577 (10)	0.0515 (10)	0.0409 (8)	0.0034 (8)	−0.0061 (7)	−0.0074 (7)
C26	0.0755 (12)	0.0423 (10)	0.0578 (10)	0.0121 (9)	0.0000 (10)	−0.0077 (8)
C27	0.0510 (9)	0.0427 (10)	0.0696 (11)	0.0087 (8)	0.0065 (9)	0.0040 (8)
C28	0.0469 (8)	0.0447 (9)	0.0677 (11)	0.0027 (7)	−0.0152 (8)	0.0085 (8)
C29	0.0408 (7)	0.0416 (8)	0.0520 (8)	−0.0023 (7)	−0.0157 (6)	0.0003 (7)
C30A	0.0498 (12)	0.0332 (10)	0.0420 (10)	0.0037 (9)	−0.0042 (9)	0.0018 (9)
C31A	0.0383 (10)	0.0425 (12)	0.0610 (14)	0.0089 (9)	−0.0063 (10)	0.0023 (11)
C32A	0.097 (2)	0.0362 (12)	0.0577 (15)	0.0179 (13)	−0.0066 (15)	−0.0083 (11)
N12A	0.0601 (13)	0.0525 (13)	0.0757 (16)	0.0089 (12)	0.0031 (12)	0.0046 (13)
C30B	0.056 (3)	0.0187 (19)	0.0347 (19)	−0.0102 (17)	−0.0197 (18)	0.0106 (15)
C32B	0.042 (2)	0.049 (3)	0.099 (5)	0.027 (2)	−0.031 (3)	−0.014 (3)
N12B	0.0305 (19)	0.068 (4)	0.061 (3)	−0.004 (2)	−0.0249 (19)	0.010 (3)

Geometric parameters (Å, º)

Co1—N1	1.8885 (12)	Co2—N9	1.8962 (14)
Co1—N2	1.8893 (14)	Co2—N10	1.9002 (14)
Co1—N3	1.8949 (12)	Co2—C30A	2.0370 (7)
Co1—N4	1.8985 (14)	Co2—N11	2.0552 (14)
Co1—N5	2.0330 (13)	Co2—C30B	2.0755 (6)
Co1—C14	2.0665 (18)	O5—N7	1.3648 (19)
O1—N1	1.3353 (17)	O6—N8	1.3343 (18)
O2—N2	1.3297 (17)	O7—N9	1.3782 (18)
O3—N3	1.3475 (17)	O8—N10	1.3427 (18)
O4—N4	1.3422 (18)	N7—C17	1.286 (3)
N1—C1	1.297 (2)	N8—C18	1.315 (2)
N2—C2	1.311 (2)	N9—C19	1.271 (2)
N3—C3	1.293 (2)	N10—C20	1.301 (2)
N4—C4	1.294 (2)	N11—C29	1.327 (2)
N5—C9	1.349 (2)	N11—C25	1.334 (2)
N5—C13	1.359 (2)	C17—C18	1.463 (3)
N6—C15	1.139 (2)	C17—C21	1.493 (3)
C1—C2	1.468 (2)	C18—C22	1.496 (3)
C1—C5	1.498 (3)	C19—C23	1.477 (3)
C2—C6	1.486 (2)	C19—C20	1.482 (2)
C3—C4	1.474 (2)	C20—C24	1.474 (3)
C3—C7	1.499 (2)	C25—C26	1.351 (3)
C4—C8	1.494 (2)	C26—C27	1.384 (3)
C9—C10	1.383 (3)	C27—C28	1.368 (3)
C10—C11	1.363 (3)	C28—C29	1.375 (3)
C11—C12	1.372 (3)	C30A—C31A	1.4534 (6)
C12—C13	1.380 (3)	C30A—C32A	1.5199 (7)
C14—C15	1.440 (2)	C31A—N12A	1.1534 (6)
C14—C16	1.489 (3)	C30B—C31B	1.4533 (6)
Co2—N8	1.8826 (14)	C30B—C32B	1.5200 (6)
Co2—N7	1.8957 (14)	C31B—N12B	1.1534 (6)
N1—Co1—N2	81.61 (6)	N9—Co2—N10	80.14 (6)
N1—Co1—N3	179.41 (5)	N8—Co2—C30A	84.21 (5)
N2—Co1—N3	98.88 (6)	N7—Co2—C30A	84.22 (5)
N1—Co1—N4	98.15 (6)	N9—Co2—C30A	96.34 (5)
N2—Co1—N4	177.39 (6)	N10—Co2—C30A	96.03 (5)
N3—Co1—N4	81.38 (6)	N8—Co2—N11	90.08 (6)
N1—Co1—N5	90.58 (6)	N7—Co2—N11	90.14 (6)
N2—Co1—N5	88.22 (6)	N9—Co2—N11	89.36 (6)
N3—Co1—N5	89.77 (6)	N10—Co2—N11	89.73 (6)
N4—Co1—N5	89.18 (6)	C30A—Co2—N11	172.50 (4)
N1—Co1—C14	92.71 (7)	N8—Co2—C30B	95.08 (5)
N2—Co1—C14	92.30 (7)	N7—Co2—C30B	99.64 (5)
N3—Co1—C14	86.94 (7)	N9—Co2—C30B	80.80 (5)
N4—Co1—C14	90.31 (7)	N10—Co2—C30B	84.99 (5)
N5—Co1—C14	176.71 (6)	C30A—Co2—C30B	17.737 (19)
C1—N1—O1	119.54 (13)	N11—Co2—C30B	169.50 (4)
C1—N1—Co1	116.83 (11)	C17—N7—O5	121.63 (14)
O1—N1—Co1	123.40 (10)	C17—N7—Co2	116.85 (12)
C2—N2—O2	121.34 (13)	O5—N7—Co2	121.40 (12)
C2—N2—Co1	116.27 (11)	C18—N8—O6	121.04 (14)
O2—N2—Co1	122.38 (10)	C18—N8—Co2	115.89 (12)
C3—N3—O3	120.18 (12)	O6—N8—Co2	123.03 (11)
C3—N3—Co1	116.78 (10)	C19—N9—O7	118.66 (14)
O3—N3—Co1	123.04 (10)	C19—N9—Co2	118.69 (12)
C4—N4—O4	120.15 (13)	O7—N9—Co2	122.62 (11)
C4—N4—Co1	116.38 (11)	C20—N10—O8	120.45 (14)
O4—N4—Co1	123.38 (10)	C20—N10—Co2	117.12 (11)
C9—N5—C13	116.24 (14)	O8—N10—Co2	122.16 (11)
C9—N5—Co1	122.26 (11)	C29—N11—C25	117.40 (15)
C13—N5—Co1	121.49 (11)	C29—N11—Co2	120.60 (12)
N1—C1—C2	112.60 (14)	C25—N11—Co2	121.97 (11)
N1—C1—C5	124.88 (16)	N7—C17—C18	112.59 (16)
C2—C1—C5	122.47 (17)	N7—C17—C21	123.41 (18)
N2—C2—C1	112.53 (14)	C18—C17—C21	123.99 (18)
N2—C2—C6	124.51 (15)	N8—C18—C17	112.91 (16)
C1—C2—C6	122.95 (15)	N8—C18—C22	123.52 (17)
N3—C3—C4	112.53 (14)	C17—C18—C22	123.55 (18)
N3—C3—C7	124.49 (15)	N9—C19—C23	126.61 (17)
C4—C3—C7	122.98 (15)	N9—C19—C20	111.88 (15)
N4—C4—C3	112.88 (14)	C23—C19—C20	121.46 (17)
N4—C4—C8	124.15 (16)	N10—C20—C24	123.94 (17)
C3—C4—C8	122.97 (15)	N10—C20—C19	112.02 (15)
N5—C9—C10	122.51 (18)	C24—C20—C19	124.04 (17)
C11—C10—C9	120.1 (2)	N11—C25—C26	124.08 (17)
C10—C11—C12	118.7 (2)	C25—C26—C27	118.27 (19)
C11—C12—C13	118.98 (17)	C28—C27—C26	118.33 (18)
N5—C13—C12	123.40 (16)	C27—C28—C29	119.54 (18)
C15—C14—C16	110.86 (16)	N11—C29—C28	122.24 (17)
C15—C14—Co1	110.00 (13)	C31A—C30A—C32A	108.28 (5)
C16—C14—Co1	118.09 (12)	C31A—C30A—Co2	110.15 (5)
N6—C15—C14	176.3 (2)	C32A—C30A—Co2	114.20 (4)
N8—Co2—N7	81.62 (7)	N12A—C31A—C30A	178.17 (10)
N8—Co2—N9	99.15 (6)	C31B—C30B—C32B	108.29 (5)
N7—Co2—N9	179.08 (7)	C31B—C30B—Co2	110.56 (4)
N8—Co2—N10	179.27 (6)	C32B—C30B—Co2	115.09 (4)
N7—Co2—N10	99.08 (7)	N12B—C31B—C30B	179.87 (7)

(2-neutron) '[(R)-1-cyanoethyl](pyridine)bis(dimethylglyoximato)cobalt(III) irradiated'

Crystal data

C16H22CoDN6O4	F(000) = 108
Mr = 423.33	Dx = 0.752 Mg m^−3
Monoclinic, P21	Neutron radiation, λ = 1.06000 Å
a = 16.023 (5) Å	Cell parameters from 25 (determined by X-rays) reflections
b = 12.627 (2) Å	θ = 14 (X-ray, MoKα)–15 (X-ray, MoKα)°
c = 9.628 (2) Å	µ = 0.21 mm^−1
β = 94.23 (2)°	T = 293 K
V = 1942.6 (7) Å^3	Plate, red
Z = 4	3.0 × 3.0 × 0.6 mm

Data collection

BIX-I diffractometer	1418 reflections with I > 2σ(I)
Radiation source: JRR-3M atomic reactor	Rint = 0.076
Bent Si crystal monochromator	θmax = 42.0°, θmin = 3.1°
0.2deg ω step scan	h = −17→19
1954 measured reflections	k = −13→2
1424 independent reflections	l = −11→8

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)] = 0.132	Refine
wR(F^2) = 0.328	Calculated w = 1/[s^2(Fo^2) + ( 0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 3.30	(Δ/σ)max = −0.136
1424 reflections	Δρmax = 0.16 e Å^−3
464 parameters	Δρmin = −0.10 e Å^−3
25 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −9.99 (999)

Special details

Experimental. The crystal was obtained by slow evaporation from methanol/water.

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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	0.0201	0.8972	0.7355	0.068 (5)*
O1	0.0491	0.9442	1.0246	0.083 (4)
HO1	0.0867 (10)	0.9755 (9)	0.995 (3)	0.134 (10)
O2	−0.1067	0.7674	0.6044	0.067 (3)
O3	−0.0057	0.8463	0.4458	0.119 (7)
HO3	−0.0524 (15)	0.816 (2)	0.5133 (18)	0.126 (7)
O4	0.1436	1.0361	0.8662	0.069 (3)
N1	0.0023	0.8914	0.9271	0.075 (2)
N2	−0.0748	0.8079	0.7243	0.062 (2)
N3	0.0391	0.9030	0.5437	0.055 (2)
N4	0.1121	0.9924	0.7466	0.062 (2)
N5	−0.0588	1.0229	0.7101	0.076 (2)
C1	−0.0629	0.8397	0.9615	0.069 (3)
C2	−0.1085	0.7887	0.8417	0.075 (3)
C3	0.0987	0.9644	0.5089	0.083 (3)
C4	0.1415	1.0185	0.6298	0.075 (3)
C5	−0.0923	0.8347	1.1055	0.107 (5)
H5A	−0.051 (2)	0.880 (3)	1.182 (4)	0.129 (10)*
H5B	−0.1092 (15)	0.745 (2)	1.142 (3)	0.096 (6)*
H5C	−0.147 (3)	0.910 (4)	1.131 (4)	0.158 (13)*
C6	−0.1837	0.7215	0.8547	0.072 (3)
H6A	−0.224 (3)	0.720 (4)	0.760 (5)	0.160 (13)*
H6B	−0.2283 (14)	0.774 (2)	0.911 (2)	0.088 (6)*
H6C	−0.1672 (16)	0.637 (2)	0.882 (3)	0.101 (6)*
C7	0.1223	0.9804	0.3626	0.087 (4)
H7A	0.0838 (13)	0.915 (2)	0.300 (2)	0.085 (5)*
H7B	0.1956 (17)	0.968 (3)	0.358 (3)	0.111 (8)*
H7C	0.1444 (19)	1.033 (3)	0.330 (3)	0.117 (8)*
C8	0.2112	1.0958	0.6169	0.089 (4)
H8A	0.2130 (18)	1.133 (3)	0.719 (3)	0.114 (8)*
H8B	0.220 (2)	1.135 (3)	0.534 (4)	0.133 (10)*
H8C	0.274 (2)	1.065 (4)	0.611 (4)	0.145 (11)*
C9	−0.0579	1.1035	0.8023	0.084 (3)
H9	−0.008 (2)	1.111 (3)	0.884 (4)	0.128 (10)*
C10	−0.1129	1.1879	0.7875	0.115 (5)
H10	−0.0995 (17)	1.264 (3)	0.856 (3)	0.105 (7)*
C11	−0.1673	1.1954	0.6723	0.114 (5)
H11	−0.201 (2)	1.264 (2)	0.643 (7)	0.30 (4)*
C12	−0.1688	1.1154	0.5755	0.088 (4)
H12	−0.199 (2)	1.114 (3)	0.481 (4)	0.138 (11)*
C13	−0.1146	1.0312	0.5974	0.091 (4)
H13	−0.1075 (15)	0.960 (2)	0.535 (3)	0.095 (6)*
C14	0.1014	0.7699	0.7492	0.070 (2)*
C15	0.1645	0.7861	0.8617	0.078 (3)*
C16	0.0651	0.6616	0.7551	0.098 (4)*
H16A	0.031 (2)	0.644 (4)	0.660 (4)	0.143 (11)*
H16B	0.0270 (19)	0.647 (3)	0.836 (3)	0.116 (8)*
H16C	0.114 (2)	0.596 (3)	0.759 (4)	0.131 (10)*
N6	0.2154	0.7932	0.9501	0.093 (2)*
D14	0.1348 (8)	0.7796 (11)	0.6548 (11)	0.104 (4)*
Co2	0.4903	0.7263	0.7490	0.068 (6)*
O5	0.4600	0.6773	0.4601	0.122 (5)
HO5	0.3991 (8)	0.6313 (14)	0.5380 (14)	0.062 (4)
O6	0.6172	0.8557	0.8819	0.085 (5)
O7	0.5191	0.7713	1.0421	0.061 (3)
HO7	0.5688 (14)	0.8265 (13)	0.9740 (17)	0.081 (5)
O8	0.3639	0.5934	0.6179	0.103 (6)
N7	0.5095	0.7316	0.5572	0.064 (2)
N8	0.5844	0.8160	0.7616	0.072 (2)
N9	0.4704	0.7187	0.9404	0.083 (3)
N10	0.3955	0.6354	0.7387	0.083 (3)
N11	0.5673	0.5964	0.7738	0.057 (2)
C17	0.5741	0.7836	0.5240	0.067 (3)
C18	0.6185	0.8351	0.6440	0.069 (3)
C19	0.4110	0.6605	0.9768	0.063 (3)
C20	0.3663	0.6074	0.8558	0.091 (4)
C21	0.6014	0.7889	0.3792	0.083 (4)
H21A	0.6638 (13)	0.8216 (16)	0.3814 (2)	0.124*
H21B	0.5588 (11)	0.8387 (16)	0.3163 (13)	0.124*
H21C	0.6013 (12)	0.7102 (15)	0.3352 (11)	0.124*
C22	0.6933	0.9047	0.6335	0.100 (4)
H22A	0.6993 (17)	0.937 (2)	0.740 (3)	0.102 (7)*
H22B	0.6879 (17)	0.950 (3)	0.534 (3)	0.108 (8)*
H22C	0.7538 (18)	0.867 (3)	0.611 (3)	0.114 (8)*
C23	0.3882	0.6410	1.1204	0.073 (3)
H23A	0.4269 (16)	0.657 (3)	1.190 (3)	0.105 (7)*
H23B	0.3284 (16)	0.683 (2)	1.126 (3)	0.103 (7)*
H23C	0.3956 (10)	0.5628 (14)	1.1577 (16)	0.057 (3)*
C24	0.2963	0.5329	0.8666	0.094 (4)
H24A	0.2565 (15)	0.541 (2)	0.783 (3)	0.093 (6)*
H24B	0.2497 (18)	0.569 (3)	0.943 (3)	0.114 (8)*
H24C	0.309 (3)	0.455 (5)	0.935 (5)	0.183 (17)*
C25	0.5600	0.5136	0.6880	0.100 (5)
H25	0.5113 (14)	0.525 (2)	0.612 (2)	0.106 (8)*
C26	0.6076	0.4253	0.7025	0.087 (4)
H26	0.5961 (14)	0.366 (2)	0.634 (3)	0.109 (8)*
C27	0.6720	0.4234	0.8066	0.100 (5)
H27	0.7061 (11)	0.3572 (17)	0.8055 (19)	0.079 (5)*
C28	0.6817	0.5089	0.8935	0.111 (4)
H28	0.7367 (12)	0.5205 (18)	0.991 (2)	0.087 (6)*
C29	0.6283	0.5938	0.8749	0.071 (3)
H29	0.6372 (13)	0.661 (2)	0.937 (2)	0.100 (7)*
C30A	0.4252	0.8627	0.7081	0.066 (3)*	0.697 (9)
C31A	0.3446	0.8393	0.6352	0.063 (2)*	0.697 (9)
C32A	0.4101	0.9278	0.8366	0.071 (3)*	0.697 (9)
H32A	0.4616 (3)	0.9352 (16)	0.8933 (13)	0.107*	0.697 (9)
H32B	0.3695 (11)	0.8927 (10)	0.8890 (13)	0.107*	0.697 (9)
H32C	0.3896 (14)	0.9966 (7)	0.80869 (7)	0.107*	0.697 (9)
N12A	0.2809	0.8230	0.5752	0.115 (4)*	0.697 (9)
D30A	0.4660 (14)	0.919 (2)	0.648 (2)	0.104 (6)*	0.697 (9)
C30B	0.4034	0.8477	0.7569	0.066 (3)*	0.303 (9)
C31B	0.3390	0.8380	0.6433	0.063 (2)*	0.303 (9)
C32B	0.4396	0.9589	0.7538	0.071 (3)*	0.303 (9)
H32D	0.479 (3)	0.9689 (15)	0.833 (3)	0.107*	0.303 (9)
H32E	0.3952 (4)	1.00979 (2)	0.756 (6)	0.107*	0.303 (9)
H32F	0.468 (3)	0.9682 (15)	0.670 (3)	0.107*	0.303 (9)
N12B	0.2879	0.8302	0.5531	0.115 (4)*	0.303 (9)
D30B	0.3684 (12)	0.8423 (18)	0.8490 (14)	0.066 (8)*	0.303 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.086 (6)	0.127 (9)	0.034 (3)	0.018 (7)	−0.016 (4)	−0.044 (4)
HO1	0.17 (2)	0.062 (13)	0.169 (19)	−0.010 (14)	0.015 (18)	0.065 (12)
O2	0.069 (5)	0.061 (6)	0.070 (5)	−0.031 (5)	−0.006 (5)	−0.016 (5)
O3	0.090 (8)	0.173 (17)	0.098 (9)	0.009 (10)	0.030 (7)	0.024 (10)
HO3	0.139 (14)	0.173 (15)	0.058 (7)	0.052 (14)	−0.037 (9)	0.064 (8)
O4	0.078 (5)	0.025 (5)	0.099 (7)	0.001 (4)	−0.027 (5)	0.022 (5)
N1	0.079 (4)	0.085 (5)	0.060 (3)	0.001 (4)	0.003 (3)	−0.020 (3)
N2	0.063 (3)	0.044 (3)	0.079 (4)	−0.019 (3)	−0.003 (3)	−0.006 (3)
N3	0.059 (3)	0.057 (4)	0.049 (3)	0.006 (3)	−0.006 (2)	0.005 (3)
N4	0.063 (3)	0.051 (4)	0.070 (3)	0.002 (3)	−0.006 (3)	0.005 (3)
N5	0.061 (3)	0.103 (6)	0.065 (3)	0.012 (4)	0.007 (3)	−0.009 (4)
C1	0.061 (4)	0.115 (8)	0.031 (3)	0.019 (5)	0.012 (3)	0.013 (4)
C2	0.089 (6)	0.058 (6)	0.078 (5)	−0.007 (5)	0.002 (5)	−0.021 (5)
C3	0.050 (4)	0.115 (9)	0.087 (6)	−0.019 (5)	0.023 (4)	−0.026 (6)
C4	0.069 (5)	0.049 (6)	0.108 (7)	−0.018 (4)	0.017 (5)	−0.018 (5)
C5	0.122 (8)	0.154 (12)	0.048 (4)	0.022 (9)	0.036 (5)	−0.001 (7)
C6	0.061 (5)	0.046 (5)	0.110 (7)	−0.017 (4)	0.005 (5)	−0.007 (5)
C7	0.122 (8)	0.059 (7)	0.079 (6)	0.001 (7)	−0.002 (6)	−0.005 (5)
C8	0.079 (6)	0.023 (5)	0.164 (11)	0.003 (4)	−0.009 (6)	0.013 (6)
C9	0.087 (6)	0.063 (6)	0.099 (7)	0.025 (5)	−0.020 (5)	0.016 (5)
C10	0.159 (9)	0.104 (10)	0.074 (6)	0.055 (8)	−0.041 (7)	−0.009 (6)
C11	0.136 (9)	0.039 (7)	0.169 (12)	−0.013 (7)	0.028 (9)	0.018 (7)
C12	0.091 (6)	0.070 (7)	0.097 (6)	0.018 (6)	−0.035 (5)	0.022 (5)
C13	0.107 (7)	0.094 (8)	0.073 (6)	0.030 (7)	0.016 (5)	−0.005 (6)
O5	0.214 (14)	0.050 (7)	0.110 (8)	0.043 (8)	0.070 (8)	0.053 (5)
HO5	0.064 (7)	0.063 (10)	0.052 (6)	−0.026 (6)	−0.044 (5)	0.016 (6)
O6	0.049 (4)	0.146 (13)	0.057 (5)	−0.018 (7)	−0.027 (4)	0.018 (7)
O7	0.089 (6)	0.045 (5)	0.045 (4)	−0.030 (4)	−0.019 (4)	−0.011 (4)
HO7	0.135 (14)	0.046 (8)	0.067 (7)	−0.026 (9)	0.035 (9)	−0.042 (6)
O8	0.109 (9)	0.141 (14)	0.061 (7)	−0.033 (10)	0.017 (6)	0.004 (8)
N7	0.111 (5)	0.034 (4)	0.046 (3)	0.009 (3)	−0.006 (3)	−0.003 (2)
N8	0.076 (4)	0.079 (5)	0.059 (3)	0.013 (4)	−0.008 (3)	0.021 (3)
N9	0.086 (4)	0.056 (4)	0.106 (5)	−0.001 (4)	0.003 (4)	−0.035 (4)
N10	0.072 (4)	0.103 (6)	0.072 (4)	−0.014 (4)	−0.008 (3)	−0.014 (5)
N11	0.076 (3)	0.024 (3)	0.068 (3)	0.006 (3)	−0.006 (3)	−0.008 (3)
C17	0.060 (4)	0.067 (6)	0.074 (5)	−0.016 (4)	0.002 (4)	0.021 (4)
C18	0.100 (7)	0.047 (5)	0.061 (5)	0.012 (5)	0.013 (5)	−0.011 (4)
C19	0.083 (5)	0.051 (5)	0.055 (4)	−0.003 (5)	0.004 (4)	0.022 (4)
C20	0.058 (4)	0.146 (9)	0.067 (5)	0.042 (6)	0.002 (4)	0.051 (6)
C21	0.097 (7)	0.049 (6)	0.101 (7)	0.007 (5)	0.004 (6)	0.006 (5)
C22	0.111 (8)	0.111 (10)	0.073 (6)	−0.003 (8)	−0.043 (6)	0.016 (7)
C23	0.089 (5)	0.074 (6)	0.061 (4)	0.010 (5)	0.044 (4)	0.012 (5)
C24	0.084 (6)	0.116 (10)	0.087 (6)	−0.009 (7)	0.033 (5)	−0.010 (7)
C25	0.080 (6)	0.162 (13)	0.060 (5)	−0.036 (7)	0.011 (5)	−0.029 (7)
C26	0.141 (8)	0.076 (7)	0.047 (4)	0.040 (6)	0.028 (5)	−0.008 (5)
C27	0.059 (5)	0.159 (13)	0.078 (6)	0.010 (7)	−0.027 (5)	−0.029 (8)
C28	0.108 (7)	0.071 (8)	0.146 (9)	−0.032 (6)	−0.051 (7)	−0.035 (7)
C29	0.044 (3)	0.074 (7)	0.090 (5)	0.004 (5)	−0.036 (4)	−0.017 (5)

Geometric parameters (Å, º)

Co1—N1	1.8887 (4)	Co2—N10	1.9006 (4)
Co1—N2	1.8892 (4)	Co2—C30A	2.0369 (3)
Co1—N3	1.8950 (4)	Co2—N11	2.0558 (3)
Co1—N4	1.8990 (3)	Co2—C30B	2.0761 (3)
Co1—N5	2.0327 (3)	Co2—D30A	2.64 (2)
Co1—C14	2.0671 (3)	Co2—D30B	2.68 (2)
Co1—D14	2.529 (13)	O5—N7	1.3652 (3)
O1—N1	1.3357 (3)	O6—N8	1.3339 (3)
O2—N2	1.3302 (3)	O7—N9	1.3769 (3)
O3—N3	1.3474 (3)	O8—N10	1.3429 (3)
O4—N4	1.3414 (3)	N7—C17	1.2859 (2)
N1—C1	1.2959 (3)	N8—C18	1.3153 (3)
N2—C2	1.3114 (3)	N9—C19	1.2720 (2)
N3—C3	1.2933 (2)	N10—C20	1.3011 (3)
N4—C4	1.2936 (3)	N11—C29	1.3279 (3)
N5—C9	1.3499 (2)	N11—C25	1.3323 (2)
N5—C13	1.3582 (4)	C17—C18	1.4637 (3)
C1—C2	1.4679 (3)	C17—C21	1.4931 (3)
C1—C5	1.4977 (3)	C18—C22	1.4956 (3)
C2—C6	1.4864 (3)	C19—C23	1.4765 (3)
C3—C4	1.4745 (3)	C19—C20	1.4820 (3)
C3—C7	1.4988 (3)	C20—C24	1.4734 (3)
C4—C8	1.4953 (3)	C25—C26	1.3523 (2)
C9—C10	1.3829 (2)	C26—C27	1.3846 (4)
C10—C11	1.3631 (3)	C27—C28	1.3677 (2)
C11—C12	1.3734 (2)	C28—C29	1.3751 (2)
C12—C13	1.3792 (2)	C30A—D30A	1.15 (2)
C14—D14	1.095 (11)	C30A—C31A	1.4539 (4)
C14—C15	1.4407 (4)	C30A—C32A	1.5196 (2)
C14—C16	1.4888 (2)	C31A—N12A	1.1536 (3)
C15—N6	1.1380 (3)	C30B—D30B	1.09 (2)
Co2—N8	1.8825 (3)	C30B—C31B	1.4523 (4)
Co2—N7	1.8955 (4)	C30B—C32B	1.5204 (2)
Co2—N9	1.8956 (4)	C31B—N12B	1.1529 (3)
N1—Co1—N2	81.59 (2)	N8—Co2—N11	90.09 (2)
N1—Co1—N3	179.4	N7—Co2—N11	90.123 (13)
N2—Co1—N3	98.85 (2)	N9—Co2—N11	89.386 (13)
N1—Co1—N4	98.17 (2)	N10—Co2—N11	89.69 (2)
N2—Co1—N4	177.4	C30A—Co2—N11	172.527 (2)
N3—Co1—N4	81.40 (2)	N8—Co2—C30B	95.13 (2)
N1—Co1—N5	90.593 (12)	N7—Co2—C30B	99.622 (14)
N2—Co1—N5	88.20 (2)	N9—Co2—C30B	80.814 (14)
N3—Co1—N5	89.761 (13)	N10—Co2—C30B	84.97 (2)
N4—Co1—N5	89.19 (2)	N11—Co2—C30B	169.506 (3)
N1—Co1—C14	92.717 (12)	N8—Co2—D30A	64.2 (5)
N2—Co1—C14	92.29 (2)	N7—Co2—D30A	68.7 (5)
N3—Co1—C14	86.929 (13)	N9—Co2—D30A	112.1 (5)
N4—Co1—C14	90.33 (2)	N10—Co2—D30A	116.2 (5)
N5—Co1—C14	176.7	C30A—Co2—D30A	24.5 (5)
N1—Co1—D14	116.3 (2)	N11—Co2—D30A	148.1 (5)
N2—Co1—D14	103.4 (3)	N8—Co2—D30B	104.5 (4)
N3—Co1—D14	63.3 (2)	N7—Co2—D30B	120.4 (3)
N4—Co1—D14	79.1 (3)	N9—Co2—D30B	59.9 (3)
N5—Co1—D14	151.8 (3)	N10—Co2—D30B	75.4 (4)
C14—Co1—D14	25.1 (3)	N11—Co2—D30B	147.4 (4)
C1—N1—O1	119.562 (14)	C30B—Co2—D30B	22.1 (4)
C1—N1—Co1	116.87 (2)	C17—N7—O5	121.590 (13)
O1—N1—Co1	123.343 (14)	C17—N7—Co2	116.85 (2)
C2—N2—O2	121.325 (13)	O5—N7—Co2	121.436 (14)
C2—N2—Co1	116.27 (2)	C18—N8—O6	121.096 (14)
O2—N2—Co1	122.395 (14)	C18—N8—Co2	115.880 (14)
C3—N3—O3	120.153 (14)	O6—N8—Co2	122.99 (2)
C3—N3—Co1	116.772 (14)	C19—N9—O7	118.622 (14)
O3—N3—Co1	123.073 (13)	C19—N9—Co2	118.690 (14)
C4—N4—O4	120.222 (14)	O7—N9—Co2	122.662 (14)
C4—N4—Co1	116.318 (15)	C20—N10—O8	120.428 (14)
O4—N4—Co1	123.368 (14)	C20—N10—Co2	117.13 (2)
C9—N5—C13	116.203 (10)	O8—N10—Co2	122.172 (14)
C9—N5—Co1	122.231 (14)	C29—N11—C25	117.470 (10)
C13—N5—Co1	121.557 (11)	C29—N11—Co2	120.517 (10)
N1—C1—C2	112.60 (2)	C25—N11—Co2	121.984 (15)
N1—C1—C5	124.884 (15)	N7—C17—C18	112.58 (2)
C2—C1—C5	122.470 (14)	N7—C17—C21	123.481 (14)
N2—C2—C1	112.518 (15)	C18—C17—C21	123.934 (14)
N2—C2—C6	124.527 (14)	N8—C18—C17	112.918 (15)
C1—C2—C6	122.948 (15)	N8—C18—C22	123.492 (14)
N3—C3—C4	112.490 (15)	C17—C18—C22	123.568 (14)
N3—C3—C7	124.515 (13)	N9—C19—C23	126.599 (13)
C4—C3—C7	122.994 (13)	N9—C19—C20	111.889 (14)
N4—C4—C3	112.969 (15)	C23—C19—C20	121.464 (14)
N4—C4—C8	124.103 (12)	N10—C20—C24	123.982 (14)
C3—C4—C8	122.926 (13)	N10—C20—C19	111.99 (2)
N5—C9—C10	122.516 (14)	C24—C20—C19	124.027 (13)
C11—C10—C9	120.125 (10)	N11—C25—C26	124.058 (14)
C10—C11—C12	118.622 (11)	C25—C26—C27	118.262 (10)
C11—C12—C13	118.950 (14)	C28—C27—C26	118.300 (10)
N5—C13—C12	123.482 (10)	C27—C28—C29	119.620 (15)
D14—C14—C15	104.5 (6)	N11—C29—C28	122.138 (10)
D14—C14—C16	110.5 (7)	D30A—C30A—C31A	113.4 (11)
C15—C14—C16	110.866 (7)	D30A—C30A—C32A	102.0 (12)
D14—C14—Co1	101.8 (7)	C31A—C30A—C32A	108.29 (2)
C15—C14—Co1	109.970 (12)	D30A—C30A—Co2	108.6 (12)
C16—C14—Co1	118.07 (2)	C31A—C30A—Co2	110.207 (12)
N6—C15—C14	176.269 (2)	C32A—C30A—Co2	114.210 (13)
C14—D14—Co1	53.2 (6)	N12A—C31A—C30A	178.2
N8—Co2—N7	81.65 (2)	C30A—D30A—Co2	47.0 (9)
N8—Co2—N9	99.16 (2)	D30B—C30B—C31B	103.2 (9)
N7—Co2—N9	179.055 (1)	D30B—C30B—C32B	107.1 (12)
N8—Co2—N10	179.3	C31B—C30B—C32B	108.299 (7)
N7—Co2—N10	99.04 (2)	D30B—C30B—Co2	111.8 (12)
N9—Co2—N10	80.15 (2)	C31B—C30B—Co2	110.565 (14)
N8—Co2—C30A	84.26 (2)	C32B—C30B—Co2	115.05 (2)
N7—Co2—C30A	84.228 (12)	N12B—C31B—C30B	179.9
N9—Co2—C30A	96.329 (12)	C30B—D30B—Co2	46.0 (9)
N10—Co2—C30A	96.01 (2)

(3-initial) '[(R,S)-1-cyanoethyl](piperidine)bis(dimethylglyoximato)cobalt(III) initial'

Crystal data

C16H29CoN6O4	Dx = 1.391 Mg m^−3
Mr = 428.38	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 512 reflections
a = 11.4309 (12) Å	θ = 1.3–27.5°
b = 11.6591 (6) Å	µ = 0.87 mm^−1
c = 30.701 (3) Å	T = 293 K
V = 4091.6 (6) Å^3	Plate, dark red
Z = 8	0.3 × 0.3 × 0.1 mm
F(000) = 1808

Data collection

Bluker SMART CCD diffractometer	8265 independent reflections
Radiation source: rotate anode	7379 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.114
ω scans	θmax = 27.5°, θmin = 1.3°
Absorption correction: empirical (using intensity measurements) (SADABS: sheldrick, 1996) ?	h = −14→11
Tmin = 0.632, Tmax = 0.781	k = −11→13
15591 measured reflections	l = −38→39

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)] = 0.084	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.252	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.77	(Δ/σ)max = 0.002
8265 reflections	Δρmax = 0.80 e Å^−3
491 parameters	Δρmin = −1.34 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.10 (3)

Special details

Experimental. The crystal was obtained by slow evaporation from methanol/water.

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	1.35017 (6)	−0.00377 (7)	1.34987 (2)	0.0450 (2)
O1	1.3023 (5)	−0.0958 (5)	1.43337 (15)	0.0670 (14)
HO1	1.3019 (5)	−0.035 (10)	1.4360 (5)	0.100*
O2	1.3731 (5)	−0.1220 (5)	1.26947 (14)	0.0673 (13)
O3	1.3923 (6)	0.0875 (6)	1.26589 (17)	0.0777 (16)
HO3	1.3788 (14)	−0.045 (12)	1.2594 (6)	0.117*
O4	1.3156 (4)	0.1168 (4)	1.43008 (16)	0.0587 (11)
N1	1.3242 (5)	−0.1218 (5)	1.39171 (17)	0.0546 (13)
N2	1.3584 (5)	−0.1321 (6)	1.31224 (17)	0.0581 (13)
N3	1.3761 (5)	0.1136 (6)	1.3079 (2)	0.0619 (15)
N4	1.3405 (4)	0.1240 (5)	1.38722 (17)	0.0508 (11)
N5	1.5300 (4)	−0.0241 (5)	1.36141 (18)	0.0559 (13)
H5	1.5410	−0.1010	1.3644	0.067*
N6	1.0816 (6)	0.1927 (8)	1.3585 (3)	0.087 (2)
C1	1.3295 (5)	−0.2225 (5)	1.3779 (2)	0.0476 (12)
C2	1.3501 (6)	−0.2311 (5)	1.3313 (2)	0.0493 (12)
C3	1.3827 (5)	0.2183 (7)	1.3222 (2)	0.0581 (16)
C4	1.3613 (5)	0.2238 (6)	1.3698 (2)	0.0577 (15)
C5	1.3131 (8)	−0.3242 (7)	1.4060 (3)	0.072 (2)
H5A	1.3007	−0.3000	1.4355	0.108*
H5B	1.3816	−0.3718	1.4046	0.108*
H5C	1.2464	−0.3670	1.3961	0.108*
C6	1.3620 (7)	−0.3421 (6)	1.3073 (3)	0.0681 (19)
H6A	1.3752	−0.3270	1.2769	0.102*
H6B	1.2916	−0.3861	1.3106	0.102*
H6C	1.4269	−0.3845	1.3189	0.102*
C7	1.4100 (9)	0.3168 (10)	1.2947 (4)	0.097 (3)
H7A	1.4205	0.2918	1.2652	0.145*
H7B	1.4806	0.3525	1.3049	0.145*
H7C	1.3469	0.3710	1.2960	0.145*
C8	1.3609 (7)	0.3359 (6)	1.3931 (3)	0.072 (2)
H8A	1.3453	0.3234	1.4234	0.109*
H8B	1.3013	0.3844	1.3810	0.109*
H8C	1.4358	0.3721	1.3898	0.109*
C9	1.6086 (5)	0.0110 (8)	1.3251 (2)	0.071 (2)
H9A	1.6074	0.0939	1.3223	0.085*
H9B	1.5803	−0.0216	1.2981	0.085*
C10	1.7363 (6)	−0.0297 (8)	1.3334 (3)	0.080 (2)
H10A	1.7384	−0.1128	1.3349	0.096*
H10B	1.7859	−0.0055	1.3094	0.096*
C11	1.7804 (6)	0.0195 (9)	1.3747 (4)	0.093 (3)
H11A	1.7846	0.1023	1.3723	0.112*
H11B	1.8585	−0.0093	1.3805	0.112*
C12	1.6997 (7)	−0.0130 (11)	1.4116 (3)	0.096 (3)
H12A	1.7280	0.0213	1.4384	0.115*
H12B	1.7005	−0.0956	1.4153	0.115*
C13	1.5736 (6)	0.0273 (8)	1.4031 (3)	0.0706 (19)
H13A	1.5235	0.0038	1.4270	0.085*
H13B	1.5715	0.1103	1.4012	0.085*
C14	1.1749 (5)	0.0048 (6)	1.3333 (2)	0.0599 (15)
H14	1.1730	0.0085	1.3014	0.072*
C15	1.1243 (6)	0.1102 (7)	1.3480 (3)	0.0632 (17)
C16	1.1008 (7)	−0.0945 (9)	1.3452 (4)	0.093 (3)
H16A	1.1366	−0.1638	1.3348	0.140*
H16B	1.0250	−0.0860	1.3322	0.140*
H16C	1.0930	−0.0982	1.3763	0.140*
Co2	1.14511 (6)	−0.01110 (7)	1.12244 (2)	0.0456 (2)
O5	1.0060 (5)	0.1817 (5)	1.0966 (2)	0.0790 (16)
HO5	0.954 (6)	0.145 (4)	1.126 (3)	0.118*
O6	1.3655 (4)	−0.0804 (5)	1.08917 (17)	0.0644 (12)
O7	1.2921 (4)	−0.1909 (5)	1.15241 (19)	0.0685 (14)
HO7	1.349 (5)	−0.146 (4)	1.117 (3)	0.103*
O8	0.9247 (5)	0.0609 (6)	1.1553 (2)	0.0793 (17)
N7	1.1034 (5)	0.1150 (6)	1.08931 (19)	0.0571 (13)
N8	1.2757 (4)	−0.0073 (5)	1.08527 (17)	0.0540 (12)
N9	1.1896 (4)	−0.1369 (5)	1.15770 (17)	0.0507 (11)
N10	1.0144 (4)	−0.0147 (5)	1.15940 (17)	0.0534 (11)
N11	1.0561 (4)	−0.1277 (4)	1.08190 (16)	0.0458 (10)
H11	1.0182	−0.1763	1.1003	0.055*
N12	1.3942 (6)	0.2127 (7)	1.1305 (3)	0.084 (2)
C17	1.1738 (7)	0.1426 (7)	1.0575 (2)	0.0633 (17)
C18	1.2769 (6)	0.0665 (7)	1.0552 (2)	0.0610 (17)
C19	1.1177 (6)	−0.1628 (7)	1.1889 (2)	0.0606 (17)
C20	1.0126 (6)	−0.0898 (7)	1.1895 (2)	0.0603 (15)
C21	1.1488 (9)	0.2425 (8)	1.0271 (3)	0.082 (2)
H21A	1.0768	0.2787	1.0355	0.123*
H21B	1.1423	0.2149	0.9977	0.123*
H21C	1.2115	0.2971	1.0289	0.123*
C22	1.3739 (8)	0.0879 (10)	1.0229 (3)	0.091 (3)
H22A	1.4330	0.0299	1.0261	0.137*
H22B	1.4076	0.1620	1.0282	0.137*
H22C	1.3428	0.0853	0.9939	0.137*
C23	1.1433 (9)	−0.2586 (8)	1.2197 (3)	0.081 (2)
H23A	1.2171	−0.2927	1.2123	0.122*
H23B	1.0827	−0.3153	1.2177	0.122*
H23C	1.1467	−0.2293	1.2489	0.122*
C24	0.9154 (8)	−0.1001 (11)	1.2216 (3)	0.091 (3)
H24A	0.8569	−0.0432	1.2155	0.136*
H24B	0.9454	−0.0885	1.2505	0.136*
H24C	0.8812	−0.1751	1.2196	0.136*
C25	0.9624 (6)	−0.0763 (6)	1.0540 (2)	0.0593 (15)
H25A	0.9981	−0.0238	1.0334	0.071*
H25B	0.9098	−0.0323	1.0723	0.071*
C26	0.8933 (6)	−0.1643 (8)	1.0295 (3)	0.073 (2)
H26A	0.8519	−0.2126	1.0501	0.088*
H26B	0.8354	−0.1258	1.0116	0.088*
C27	0.9658 (8)	−0.2361 (9)	1.0019 (3)	0.082 (2)
H27A	1.0013	−0.1900	0.9791	0.098*
H27B	0.9182	−0.2948	0.9882	0.098*
C28	1.0635 (7)	−0.2937 (8)	1.0303 (3)	0.081 (2)
H28A	1.0281	−0.3459	1.0510	0.097*
H28B	1.1156	−0.3375	1.0117	0.097*
C29	1.1322 (6)	−0.2029 (6)	1.0543 (2)	0.0579 (15)
H29A	1.1900	−0.2399	1.0726	0.069*
H29B	1.1735	−0.1557	1.0333	0.069*
C30	1.2322 (7)	0.0931 (8)	1.1665 (3)	0.072 (2)
H30	1.2756	0.0388	1.1847	0.086*
C31	1.3218 (6)	0.1594 (7)	1.1461 (2)	0.0633 (18)
C32	1.1676 (13)	0.1594 (12)	1.1970 (3)	0.119 (5)
H32A	1.1087	0.1122	1.2103	0.178*
H32B	1.1310	0.2226	1.1823	0.178*
H32C	1.2195	0.1881	1.2191	0.178*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0322 (3)	0.0484 (4)	0.0543 (4)	0.0042 (3)	0.0069 (2)	−0.0008 (3)
O1	0.067 (3)	0.082 (4)	0.052 (2)	−0.001 (3)	0.013 (2)	−0.003 (2)
O2	0.078 (3)	0.071 (3)	0.053 (2)	0.000 (3)	0.009 (2)	0.002 (2)
O3	0.084 (4)	0.087 (4)	0.062 (3)	0.003 (3)	0.021 (3)	0.011 (3)
O4	0.047 (2)	0.061 (3)	0.067 (3)	−0.0028 (19)	0.009 (2)	−0.017 (2)
N1	0.045 (3)	0.065 (4)	0.053 (3)	−0.006 (2)	0.008 (2)	0.002 (2)
N2	0.041 (3)	0.081 (4)	0.052 (3)	0.003 (3)	0.005 (2)	−0.013 (2)
N3	0.044 (3)	0.068 (4)	0.074 (4)	0.008 (2)	0.014 (2)	0.013 (3)
N4	0.030 (2)	0.059 (3)	0.064 (3)	0.0039 (19)	0.011 (2)	−0.014 (2)
N5	0.034 (2)	0.061 (4)	0.072 (3)	0.007 (2)	0.004 (2)	0.000 (2)
N6	0.061 (4)	0.083 (6)	0.117 (6)	0.028 (4)	−0.010 (4)	−0.009 (4)
C1	0.040 (3)	0.039 (3)	0.065 (3)	−0.0010 (19)	−0.001 (2)	0.002 (2)
C2	0.044 (3)	0.037 (3)	0.067 (3)	0.006 (2)	−0.001 (3)	−0.010 (2)
C3	0.041 (3)	0.062 (4)	0.071 (4)	0.001 (2)	0.008 (3)	0.017 (3)
C4	0.031 (3)	0.054 (4)	0.088 (4)	0.001 (2)	0.009 (3)	−0.003 (3)
C5	0.071 (5)	0.066 (5)	0.079 (5)	−0.017 (3)	−0.006 (4)	0.004 (4)
C6	0.065 (4)	0.049 (4)	0.090 (5)	−0.002 (3)	0.001 (4)	−0.032 (3)
C7	0.070 (5)	0.095 (8)	0.125 (8)	0.001 (5)	0.023 (5)	0.048 (6)
C8	0.054 (4)	0.050 (4)	0.114 (6)	−0.009 (3)	0.007 (4)	−0.013 (3)
C9	0.038 (3)	0.089 (6)	0.085 (4)	0.014 (3)	0.014 (3)	−0.003 (4)
C10	0.040 (3)	0.067 (5)	0.132 (7)	0.011 (3)	0.028 (4)	−0.006 (4)
C11	0.031 (3)	0.083 (6)	0.166 (9)	0.004 (3)	−0.005 (4)	−0.017 (6)
C12	0.058 (4)	0.123 (9)	0.106 (6)	0.027 (5)	−0.020 (4)	−0.023 (6)
C13	0.046 (3)	0.078 (5)	0.088 (4)	−0.001 (3)	−0.006 (3)	−0.016 (4)
C14	0.035 (2)	0.056 (4)	0.089 (4)	0.001 (3)	−0.007 (2)	0.014 (3)
C15	0.035 (3)	0.071 (5)	0.083 (5)	0.012 (3)	−0.005 (3)	0.007 (3)
C16	0.044 (4)	0.087 (7)	0.150 (9)	0.001 (4)	−0.006 (5)	−0.024 (6)
Co2	0.0284 (3)	0.0500 (4)	0.0584 (4)	−0.0004 (3)	0.0015 (3)	−0.0021 (3)
O5	0.065 (3)	0.075 (4)	0.097 (4)	0.034 (3)	0.005 (3)	0.005 (3)
O6	0.0304 (19)	0.076 (3)	0.086 (3)	0.0069 (18)	0.009 (2)	−0.012 (2)
O7	0.042 (2)	0.075 (4)	0.089 (4)	0.019 (2)	−0.010 (2)	−0.001 (3)
O8	0.047 (3)	0.096 (5)	0.095 (4)	0.036 (3)	0.017 (2)	0.011 (3)
N7	0.039 (2)	0.063 (4)	0.069 (3)	0.011 (2)	−0.001 (2)	0.003 (3)
N8	0.0292 (19)	0.068 (4)	0.065 (3)	−0.008 (2)	0.0014 (18)	−0.005 (3)
N9	0.034 (2)	0.053 (3)	0.065 (3)	0.0035 (19)	−0.006 (2)	0.005 (2)
N10	0.035 (2)	0.053 (3)	0.072 (3)	0.005 (2)	0.0039 (19)	−0.004 (2)
N11	0.034 (2)	0.045 (3)	0.058 (3)	−0.0085 (18)	−0.0057 (19)	−0.0013 (19)
N12	0.051 (3)	0.070 (5)	0.130 (6)	−0.011 (3)	−0.005 (4)	−0.020 (4)
C17	0.065 (4)	0.061 (4)	0.064 (4)	−0.015 (3)	−0.006 (3)	0.011 (3)
C18	0.047 (3)	0.075 (5)	0.061 (3)	−0.026 (3)	0.005 (3)	−0.019 (3)
C19	0.053 (4)	0.070 (5)	0.059 (3)	−0.009 (3)	−0.002 (3)	0.014 (3)
C20	0.050 (3)	0.065 (4)	0.066 (4)	−0.011 (3)	0.005 (3)	−0.001 (3)
C21	0.096 (6)	0.080 (6)	0.070 (4)	−0.013 (5)	−0.018 (4)	0.010 (4)
C22	0.058 (4)	0.128 (9)	0.087 (5)	−0.023 (5)	0.024 (4)	−0.002 (5)
C23	0.085 (6)	0.077 (6)	0.083 (5)	−0.009 (5)	−0.014 (4)	0.011 (4)
C24	0.064 (5)	0.110 (8)	0.099 (6)	−0.009 (5)	0.024 (4)	0.000 (5)
C25	0.046 (3)	0.049 (4)	0.083 (4)	0.000 (2)	−0.009 (3)	0.003 (3)
C26	0.045 (3)	0.084 (6)	0.090 (5)	−0.010 (3)	−0.020 (3)	0.002 (4)
C27	0.069 (5)	0.096 (7)	0.080 (4)	−0.037 (4)	−0.005 (4)	−0.018 (4)
C28	0.065 (4)	0.081 (6)	0.097 (5)	−0.013 (4)	−0.003 (4)	−0.043 (5)
C29	0.046 (3)	0.049 (4)	0.079 (4)	0.005 (2)	−0.012 (3)	−0.012 (3)
C30	0.066 (5)	0.080 (6)	0.070 (4)	−0.018 (4)	−0.003 (3)	−0.008 (4)
C31	0.045 (3)	0.065 (5)	0.080 (4)	−0.001 (3)	−0.008 (3)	−0.029 (3)
C32	0.131 (10)	0.136 (11)	0.089 (6)	−0.071 (9)	0.033 (6)	−0.044 (7)

Geometric parameters (Å, º)

Co1—N4	1.883 (5)	Co2—N7	1.850 (6)
Co1—N2	1.892 (6)	Co2—N10	1.876 (5)
Co1—N3	1.902 (6)	Co2—N8	1.879 (5)
Co1—N1	1.906 (6)	Co2—N9	1.893 (5)
Co1—C14	2.070 (5)	Co2—C30	2.072 (8)
Co1—N5	2.100 (5)	Co2—N11	2.106 (5)
O1—N1	1.338 (7)	O5—N7	1.377 (7)
O2—N2	1.329 (7)	O6—N8	1.340 (7)
O3—N3	1.339 (8)	O7—N9	1.340 (7)
O4—N4	1.349 (7)	O8—N10	1.358 (7)
N1—C1	1.250 (9)	N7—C17	1.306 (9)
N2—C2	1.297 (9)	N8—C18	1.262 (10)
N3—C3	1.299 (11)	N9—C19	1.298 (9)
N4—C4	1.303 (9)	N10—C20	1.272 (9)
N5—C9	1.488 (9)	N11—C25	1.496 (8)
N5—C13	1.498 (9)	N11—C29	1.498 (8)
N6—C15	1.126 (11)	N12—C31	1.141 (11)
C1—C2	1.454 (9)	C17—C18	1.477 (12)
C1—C5	1.478 (10)	C17—C21	1.519 (10)
C2—C6	1.495 (8)	C18—C22	1.508 (9)
C3—C7	1.459 (11)	C19—C20	1.472 (11)
C3—C4	1.482 (10)	C19—C23	1.492 (11)
C4—C8	1.490 (10)	C20—C24	1.492 (10)
C9—C10	1.555 (9)	C25—C26	1.499 (10)
C10—C11	1.481 (14)	C26—C27	1.452 (13)
C11—C12	1.509 (15)	C27—C28	1.568 (14)
C12—C13	1.539 (10)	C28—C29	1.509 (9)
C14—C15	1.431 (11)	C30—C32	1.422 (14)
C14—C16	1.479 (12)	C30—C31	1.427 (11)
N4—Co1—N2	179.5 (2)	N7—Co2—N10	98.4 (2)
N4—Co1—N3	81.5 (3)	N7—Co2—N8	81.5 (3)
N2—Co1—N3	98.5 (3)	N10—Co2—N8	179.8 (3)
N4—Co1—N1	98.7 (3)	N7—Co2—N9	178.2 (3)
N2—Co1—N1	81.3 (3)	N10—Co2—N9	81.4 (2)
N3—Co1—N1	179.7 (3)	N8—Co2—N9	98.8 (2)
N4—Co1—C14	93.1 (3)	N7—Co2—C30	91.0 (3)
N2—Co1—C14	86.4 (3)	N10—Co2—C30	90.1 (3)
N3—Co1—C14	87.1 (3)	N8—Co2—C30	90.0 (3)
N1—Co1—C14	92.8 (3)	N9—Co2—C30	87.3 (3)
N4—Co1—N5	92.5 (2)	N7—Co2—N11	93.7 (2)
N2—Co1—N5	88.0 (2)	N10—Co2—N11	87.6 (2)
N3—Co1—N5	92.4 (2)	N8—Co2—N11	92.3 (2)
N1—Co1—N5	87.5 (2)	N9—Co2—N11	88.1 (2)
C14—Co1—N5	174.2 (3)	C30—Co2—N11	175.1 (3)
C1—N1—O1	123.1 (6)	C17—N7—O5	118.7 (6)
C1—N1—Co1	116.2 (4)	C17—N7—Co2	116.7 (5)
O1—N1—Co1	120.6 (5)	O5—N7—Co2	124.6 (5)
C2—N2—O2	122.2 (5)	C18—N8—O6	119.4 (5)
C2—N2—Co1	115.1 (4)	C18—N8—Co2	118.0 (5)
O2—N2—Co1	122.7 (5)	O6—N8—Co2	122.7 (4)
C3—N3—O3	122.0 (6)	C19—N9—O7	122.3 (6)
C3—N3—Co1	117.2 (5)	C19—N9—Co2	115.6 (5)
O3—N3—Co1	120.7 (5)	O7—N9—Co2	122.0 (4)
C4—N4—O4	119.7 (5)	C20—N10—O8	120.1 (5)
C4—N4—Co1	116.4 (5)	C20—N10—Co2	117.8 (5)
O4—N4—Co1	123.8 (4)	O8—N10—Co2	122.0 (4)
C9—N5—C13	109.2 (6)	C25—N11—C29	109.0 (5)
C9—N5—Co1	115.7 (4)	C25—N11—Co2	115.1 (4)
C13—N5—Co1	115.1 (4)	C29—N11—Co2	115.6 (3)
N1—C1—C2	114.0 (5)	N7—C17—C18	112.3 (6)
N1—C1—C5	123.3 (6)	N7—C17—C21	122.2 (8)
C2—C1—C5	122.7 (6)	C18—C17—C21	125.5 (7)
N2—C2—C1	113.2 (5)	N8—C18—C17	111.5 (6)
N2—C2—C6	122.8 (6)	N8—C18—C22	127.0 (8)
C1—C2—C6	124.0 (6)	C17—C18—C22	121.2 (8)
N3—C3—C7	123.9 (8)	N9—C19—C20	113.0 (6)
N3—C3—C4	111.3 (6)	N9—C19—C23	121.1 (7)
C7—C3—C4	124.8 (8)	C20—C19—C23	125.8 (7)
N4—C4—C3	113.4 (6)	N10—C20—C19	112.1 (6)
N4—C4—C8	125.8 (7)	N10—C20—C24	123.2 (7)
C3—C4—C8	120.8 (7)	C19—C20—C24	124.7 (7)
N5—C9—C10	111.2 (6)	N11—C25—C26	113.0 (6)
C11—C10—C9	109.9 (7)	C27—C26—C25	112.8 (6)
C10—C11—C12	109.8 (7)	C26—C27—C28	109.2 (7)
C11—C12—C13	111.6 (8)	C29—C28—C27	110.0 (7)
N5—C13—C12	109.6 (7)	N11—C29—C28	112.6 (6)
C15—C14—C16	111.3 (6)	C32—C30—C31	111.5 (8)
C15—C14—Co1	110.8 (5)	C32—C30—Co2	119.9 (7)
C16—C14—Co1	117.1 (5)	C31—C30—Co2	112.1 (5)
N6—C15—C14	177.5 (9)	N12—C31—C30	178.8 (8)

(3-irradiated) '[(R,S)-1-cyanoethyl](piperidine)bis(dimethylglyoximato)cobalt(III) irradiated'

Crystal data

C16H29CoN6O4	Dx = 1.383 Mg m^−3
Mr = 428.38	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 512 reflections
a = 11.4039 (2) Å	θ = 1.9–35.0°
b = 11.7354 (2) Å	µ = 0.87 mm^−1
c = 30.7446 (1) Å	T = 293 K
V = 4114.53 (10) Å^3	Plate, dark red
Z = 8	0.3 × 0.3 × 0.2 mm
F(000) = 1808

Data collection

Bluker SMART CCD diffractometer	18013 independent reflections
Radiation source: rotate anode	12035 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ω scans	θmax = 35.0°, θmin = 1.9°
Absorption correction: empirical (using intensity measurements) (SADABS: sheldrick, 1996) ?	h = −18→15
Tmin = 0.627, Tmax = 0.743	k = −17→18
70341 measured reflections	l = −49→42

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0397P)^2 + 0.4994P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.004
18013 reflections	Δρmax = 0.48 e Å^−3
629 parameters	Δρmin = −0.64 e Å^−3
12 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.007 (9)

Special details

Experimental. The crystal was obtained by slow evaporation from methanol/water.

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	0.645547 (18)	0.513260 (17)	0.877840 (7)	0.03219 (5)
N1	0.68990 (13)	0.63955 (12)	0.84352 (5)	0.0383 (3)
N2	0.51331 (13)	0.51740 (15)	0.84092 (5)	0.0443 (3)
N3	0.60389 (15)	0.38396 (13)	0.91040 (5)	0.0432 (4)
N4	0.77645 (12)	0.50871 (14)	0.91516 (4)	0.0391 (3)
O1	0.79344 (13)	0.69388 (12)	0.84901 (5)	0.0505 (3)
HO1	0.850 (3)	0.639 (3)	0.8831 (10)	0.089 (9)*
O2	0.42271 (14)	0.44469 (16)	0.84485 (6)	0.0647 (4)
O3	0.50429 (15)	0.32312 (14)	0.90327 (6)	0.0621 (4)
HO3	0.475 (3)	0.367 (3)	0.8743 (12)	0.111 (12)*
O4	0.86717 (12)	0.58097 (13)	0.91153 (5)	0.0536 (3)
C1	0.61810 (19)	0.66836 (16)	0.81292 (7)	0.0452 (5)
C2	0.51303 (19)	0.59689 (18)	0.81151 (7)	0.0487 (5)
C3	0.6738 (2)	0.35578 (16)	0.94219 (6)	0.0479 (5)
C4	0.77675 (18)	0.42995 (18)	0.94471 (6)	0.0466 (4)
C5	0.6413 (3)	0.76341 (19)	0.78155 (8)	0.0647 (6)
H5A	0.7223	0.7854	0.7833	0.097*
H5B	0.5926	0.8274	0.7887	0.097*
H5C	0.6240	0.7383	0.7525	0.097*
C6	0.4141 (3)	0.6116 (3)	0.78033 (10)	0.0836 (9)
H6A	0.3540	0.5568	0.7867	0.125*
H6B	0.4420	0.6003	0.7512	0.125*
H6C	0.3826	0.6871	0.7831	0.125*
C7	0.6473 (3)	0.25927 (19)	0.97242 (8)	0.0705 (7)
H7A	0.6020	0.2027	0.9574	0.106*
H7B	0.6037	0.2872	0.9969	0.106*
H7C	0.7194	0.2260	0.9824	0.106*
C8	0.8743 (2)	0.4126 (3)	0.97636 (8)	0.0736 (8)
H8A	0.9390	0.4610	0.9688	0.110*
H8B	0.8991	0.3344	0.9756	0.110*
H8C	0.8477	0.4311	1.0051	0.110*
N5	0.55688 (14)	0.62587 (13)	0.91958 (5)	0.0389 (3)
HN5	0.526 (2)	0.665 (2)	0.9040 (7)	0.047*
C9	0.6321 (2)	0.70237 (19)	0.94638 (8)	0.0549 (5)
H9A	0.675 (2)	0.658 (2)	0.9661 (8)	0.066*
H9B	0.691 (2)	0.736 (2)	0.9263 (8)	0.066*
C10	0.5618 (3)	0.7935 (2)	0.97005 (9)	0.0676 (7)
H10A	0.614 (3)	0.845 (3)	0.9876 (9)	0.081*
H10B	0.515 (2)	0.839 (2)	0.9467 (7)	0.081*
C11	0.4681 (3)	0.7401 (3)	0.99847 (9)	0.0696 (7)
H11A	0.502 (3)	0.701 (3)	1.0197 (10)	0.084*
H11B	0.429 (3)	0.790 (3)	1.0151 (10)	0.084*
C12	0.3919 (2)	0.6642 (3)	0.97144 (9)	0.0666 (7)
H12A	0.335 (3)	0.627 (2)	0.9892 (9)	0.080*
H12B	0.346 (3)	0.706 (2)	0.9496 (9)	0.080*
C13	0.4638 (2)	0.5747 (2)	0.94727 (9)	0.0569 (5)
H13A	0.498 (2)	0.528 (2)	0.9666 (8)	0.068*
H13B	0.421 (2)	0.536 (2)	0.9264 (8)	0.068*
C14	0.7320 (2)	0.41320 (16)	0.83316 (6)	0.0462 (4)
H14	0.776 (2)	0.469 (2)	0.8161 (7)	0.055*
C15	0.82407 (18)	0.34686 (16)	0.85340 (7)	0.0475 (5)
C16	0.6572 (3)	0.3344 (2)	0.80559 (9)	0.0735 (8)
H16A	0.612 (3)	0.379 (3)	0.7864 (12)	0.110*
H16B	0.620 (3)	0.281 (3)	0.8230 (12)	0.110*
H16C	0.705 (3)	0.289 (3)	0.7850 (12)	0.110*
N6	0.89418 (18)	0.29063 (18)	0.86949 (8)	0.0683 (6)
Co2	0.150960 (19)	1.006960 (17)	0.850366 (6)	0.03311 (5)
N7	0.12767 (16)	0.89206 (14)	0.80806 (5)	0.0455 (4)
N8	0.15765 (14)	0.87776 (11)	0.88688 (5)	0.0371 (3)
N9	0.17445 (14)	1.12090 (13)	0.89264 (5)	0.0397 (3)
N10	0.14366 (16)	1.13511 (12)	0.81353 (5)	0.0399 (3)
O5	0.11240 (18)	0.91636 (14)	0.76555 (5)	0.0646 (5)
HO5	0.123 (3)	1.036 (3)	0.7674 (11)	0.107 (11)*
O6	0.18266 (14)	0.88473 (13)	0.92989 (5)	0.0495 (3)
O7	0.19425 (15)	1.09642 (13)	0.93465 (5)	0.0541 (4)
HO7	0.187 (2)	0.957 (2)	0.9325 (8)	0.054 (7)*
O8	0.12876 (16)	1.12667 (14)	0.77029 (4)	0.0565 (4)
C17	0.11831 (17)	0.78891 (16)	0.82195 (7)	0.0463 (5)
C18	0.13814 (17)	0.77967 (14)	0.86894 (7)	0.0436 (4)
C19	0.17103 (16)	1.22561 (14)	0.87898 (6)	0.0407 (4)
C20	0.15125 (19)	1.23461 (14)	0.83216 (6)	0.0418 (4)
C21	0.0873 (2)	0.6900 (2)	0.79346 (10)	0.0703 (7)
H21A	0.1205	0.7011	0.7651	0.105*
H21B	0.0036	0.6843	0.7911	0.105*
H21C	0.1179	0.6212	0.8059	0.105*
C22	0.1406 (2)	0.66827 (17)	0.89248 (9)	0.0601 (6)
H22A	0.141 (3)	0.680 (3)	0.9244 (10)	0.090*
H22B	0.211 (3)	0.629 (3)	0.8844 (10)	0.090*
H22C	0.075 (3)	0.621 (3)	0.8857 (10)	0.090*
C23	0.1874 (2)	1.32666 (18)	0.90813 (8)	0.0582 (6)
H23A	0.2422	1.3079	0.9308	0.087*
H23B	0.1135	1.3473	0.9208	0.087*
H23C	0.2172	1.3895	0.8915	0.087*
C24	0.1412 (3)	1.34528 (17)	0.80858 (8)	0.0580 (5)
H24A	0.126 (3)	1.336 (3)	0.7799 (10)	0.087*
H24B	0.099 (3)	1.398 (3)	0.8244 (10)	0.087*
H24C	0.221 (3)	1.378 (3)	0.8032 (9)	0.087*
N11	−0.02923 (13)	1.02587 (13)	0.86077 (5)	0.0404 (3)
HN11	−0.036 (2)	1.093 (2)	0.8632 (7)	0.048*
C25	−0.10794 (18)	0.9926 (2)	0.82423 (7)	0.0525 (5)
H25A	−0.104 (2)	0.907 (2)	0.8229 (8)	0.063*
H25B	−0.074 (2)	1.020 (2)	0.7979 (8)	0.063*
C26	−0.2339 (2)	1.0314 (2)	0.83189 (11)	0.0684 (7)
H26A	−0.285 (2)	1.005 (3)	0.8060 (7)	0.082*
H26B	−0.239 (3)	1.112 (3)	0.8299 (9)	0.082*
C27	−0.2819 (2)	0.9863 (3)	0.87342 (12)	0.0811 (8)
H27A	−0.357 (3)	1.016 (3)	0.8782 (10)	0.097*
H27B	−0.293 (3)	0.896 (3)	0.8705 (11)	0.097*
C28	−0.2011 (2)	1.0186 (3)	0.91070 (11)	0.0759 (7)
H28A	−0.226 (3)	0.993 (3)	0.9364 (10)	0.091*
H28B	−0.203 (3)	1.097 (3)	0.9166 (10)	0.091*
C29	−0.07526 (19)	0.9778 (2)	0.90208 (8)	0.0581 (5)
H29A	−0.075 (2)	0.890 (3)	0.8994 (8)	0.070*
H29B	−0.025 (2)	1.009 (2)	0.9251 (8)	0.070*
C30A	0.3238 (3)	0.9991 (4)	0.83231 (12)	0.0378 (8)	0.588 (5)
H30A	0.3238	0.9953	0.8005	0.045*	0.588 (5)
C31A	0.3757 (4)	0.8911 (4)	0.84730 (16)	0.0469 (11)*	0.588 (5)
C32A	0.3998 (3)	1.0977 (4)	0.8438 (2)	0.0768 (17)	0.588 (5)
H32A	0.3656	1.1666	0.8328	0.115*	0.588 (5)
H32B	0.4761	1.0873	0.8312	0.115*	0.588 (5)
H32C	0.4069	1.1028	0.8749	0.115*	0.588 (5)
N12A	0.4183 (8)	0.8112 (7)	0.8591 (4)	0.094 (3)	0.588 (5)
C30B	0.3336 (5)	1.0032 (6)	0.84937 (19)	0.0400 (12)	0.412 (5)
H30B	0.3609	1.0543	0.8724	0.048*	0.412 (5)
C31B	0.3809 (6)	0.8942 (5)	0.8581 (2)	0.0457 (16)*	0.412 (5)
C32B	0.3875 (8)	1.0466 (7)	0.8060 (3)	0.092 (3)*	0.412 (5)
H32D	0.3712	1.1265	0.8028	0.137*	0.412 (5)
H32E	0.3537	1.0055	0.7821	0.137*	0.412 (5)
H32F	0.4708	1.0348	0.8064	0.137*	0.412 (5)
N12B	0.4180 (10)	0.8048 (9)	0.8635 (4)	0.069 (3)	0.412 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.02900 (9)	0.02938 (9)	0.03819 (10)	−0.00160 (9)	−0.00245 (8)	0.00044 (8)
N1	0.0359 (7)	0.0324 (6)	0.0465 (8)	−0.0028 (5)	0.0056 (6)	−0.0024 (6)
N2	0.0346 (7)	0.0496 (8)	0.0485 (8)	−0.0073 (7)	−0.0062 (6)	0.0001 (7)
N3	0.0456 (9)	0.0372 (7)	0.0468 (9)	−0.0049 (6)	0.0033 (7)	0.0024 (6)
N4	0.0321 (6)	0.0428 (7)	0.0425 (7)	0.0047 (6)	−0.0003 (5)	−0.0064 (7)
O1	0.0413 (7)	0.0425 (7)	0.0679 (9)	−0.0139 (6)	0.0069 (7)	−0.0013 (6)
O2	0.0463 (8)	0.0764 (10)	0.0715 (10)	−0.0284 (7)	−0.0159 (7)	0.0094 (8)
O3	0.0644 (10)	0.0523 (8)	0.0696 (10)	−0.0274 (7)	−0.0023 (8)	0.0076 (7)
O4	0.0327 (7)	0.0640 (8)	0.0640 (9)	−0.0105 (6)	−0.0070 (6)	−0.0072 (7)
C1	0.0500 (12)	0.0381 (8)	0.0474 (10)	0.0069 (8)	0.0045 (8)	0.0069 (7)
C2	0.0451 (11)	0.0531 (11)	0.0480 (10)	0.0055 (9)	−0.0099 (8)	0.0035 (9)
C3	0.0621 (13)	0.0427 (9)	0.0388 (9)	0.0128 (9)	0.0050 (9)	0.0031 (7)
C4	0.0436 (10)	0.0553 (11)	0.0408 (9)	0.0179 (9)	−0.0005 (8)	−0.0048 (8)
C5	0.0837 (17)	0.0489 (10)	0.0614 (13)	0.0010 (13)	0.0079 (13)	0.0175 (9)
C6	0.0673 (17)	0.106 (2)	0.0772 (17)	0.0039 (16)	−0.0305 (14)	0.0193 (16)
C7	0.107 (2)	0.0536 (11)	0.0509 (12)	0.0090 (15)	0.0136 (14)	0.0132 (9)
C8	0.0546 (14)	0.108 (2)	0.0577 (13)	0.0267 (14)	−0.0129 (11)	0.0057 (13)
N5	0.0326 (8)	0.0402 (7)	0.0438 (8)	0.0059 (6)	−0.0002 (6)	0.0003 (6)
C9	0.0467 (12)	0.0531 (11)	0.0648 (13)	−0.0019 (10)	0.0063 (10)	−0.0192 (9)
C10	0.0680 (15)	0.0586 (13)	0.0763 (16)	0.0079 (12)	0.0056 (13)	−0.0255 (12)
C11	0.0713 (16)	0.0828 (17)	0.0547 (13)	0.0329 (14)	0.0095 (12)	−0.0100 (12)
C12	0.0467 (12)	0.0799 (17)	0.0732 (16)	0.0111 (12)	0.0183 (11)	−0.0034 (13)
C13	0.0461 (12)	0.0572 (12)	0.0676 (14)	−0.0029 (10)	0.0159 (10)	−0.0013 (11)
C14	0.0587 (12)	0.0365 (8)	0.0433 (10)	0.0025 (8)	0.0047 (9)	−0.0039 (7)
C15	0.0429 (11)	0.0392 (8)	0.0604 (12)	−0.0010 (8)	0.0101 (9)	−0.0144 (8)
C16	0.098 (2)	0.0569 (13)	0.0658 (15)	0.0208 (15)	−0.0307 (15)	−0.0225 (11)
N6	0.0503 (10)	0.0601 (11)	0.0946 (16)	0.0165 (9)	−0.0020 (10)	−0.0231 (11)
Co2	0.03380 (10)	0.02939 (9)	0.03613 (9)	0.00262 (10)	−0.00437 (8)	0.00107 (8)
N7	0.0490 (10)	0.0413 (7)	0.0462 (9)	0.0066 (7)	−0.0054 (7)	−0.0060 (6)
N8	0.0312 (7)	0.0370 (6)	0.0432 (8)	0.0023 (6)	−0.0031 (6)	0.0056 (5)
N9	0.0410 (8)	0.0381 (7)	0.0401 (8)	−0.0030 (6)	−0.0084 (6)	0.0008 (6)
N10	0.0432 (8)	0.0403 (7)	0.0364 (7)	0.0051 (7)	−0.0014 (7)	0.0058 (5)
O5	0.0935 (14)	0.0606 (9)	0.0396 (7)	0.0079 (9)	−0.0081 (8)	−0.0084 (7)
O6	0.0541 (9)	0.0468 (7)	0.0477 (8)	0.0000 (6)	−0.0098 (6)	0.0132 (6)
O7	0.0752 (11)	0.0503 (8)	0.0368 (7)	−0.0074 (7)	−0.0134 (7)	0.0021 (6)
O8	0.0763 (11)	0.0574 (8)	0.0358 (7)	0.0021 (8)	−0.0091 (7)	0.0080 (6)
C17	0.0377 (10)	0.0385 (8)	0.0626 (12)	0.0036 (7)	−0.0074 (8)	−0.0087 (8)
C18	0.0304 (8)	0.0332 (7)	0.0670 (12)	0.0015 (7)	−0.0042 (8)	0.0043 (7)
C19	0.0395 (10)	0.0348 (7)	0.0477 (10)	−0.0036 (6)	0.0031 (8)	−0.0010 (7)
C20	0.0393 (9)	0.0351 (7)	0.0509 (10)	0.0031 (8)	0.0026 (9)	0.0085 (7)
C21	0.0675 (15)	0.0506 (12)	0.0928 (19)	0.0016 (11)	−0.0148 (14)	−0.0261 (12)
C22	0.0539 (12)	0.0361 (8)	0.0902 (17)	−0.0038 (10)	−0.0054 (13)	0.0129 (10)
C23	0.0697 (15)	0.0399 (10)	0.0649 (13)	−0.0096 (9)	0.0063 (11)	−0.0098 (9)
C24	0.0705 (15)	0.0373 (9)	0.0662 (13)	0.0037 (11)	0.0087 (13)	0.0147 (9)
N11	0.0361 (7)	0.0332 (7)	0.0520 (8)	0.0025 (6)	−0.0051 (6)	0.0024 (6)
C25	0.0459 (9)	0.0470 (10)	0.0647 (11)	−0.0030 (9)	−0.0188 (8)	−0.0007 (10)
C26	0.0428 (11)	0.0476 (12)	0.115 (2)	0.0023 (9)	−0.0289 (12)	0.0015 (12)
C27	0.0347 (10)	0.0683 (16)	0.140 (3)	0.0058 (11)	−0.0007 (13)	0.0061 (19)
C28	0.0542 (13)	0.0825 (18)	0.0912 (18)	0.0118 (14)	0.0194 (13)	0.0050 (16)
C29	0.0445 (11)	0.0729 (15)	0.0568 (11)	0.0091 (11)	0.0057 (9)	0.0105 (11)
C30A	0.0351 (16)	0.0427 (16)	0.0354 (18)	0.0060 (14)	0.0016 (14)	0.0012 (18)
C32A	0.0321 (19)	0.055 (2)	0.143 (5)	−0.0005 (16)	0.000 (2)	0.008 (3)
N12A	0.065 (5)	0.067 (4)	0.150 (8)	0.017 (4)	0.026 (5)	0.034 (4)
C30B	0.034 (2)	0.046 (2)	0.040 (3)	0.007 (2)	−0.003 (2)	0.009 (3)
N12B	0.056 (5)	0.076 (6)	0.075 (5)	0.046 (5)	0.018 (4)	0.027 (4)

Geometric parameters (Å, º)

Co1—N3	1.8789 (16)	Co2—N8	1.8881 (14)
Co1—N4	1.8835 (14)	Co2—N7	1.8923 (16)
Co1—N2	1.8881 (15)	Co2—C30A	2.049 (4)
Co1—N1	1.8883 (15)	Co2—C30B	2.083 (5)
Co1—C14	2.058 (2)	Co2—N11	2.0915 (16)
Co1—N5	2.1015 (15)	N7—C17	1.288 (3)
N1—C1	1.292 (3)	N7—O5	1.349 (2)
N1—O1	1.352 (2)	N8—C18	1.296 (2)
N2—C2	1.299 (3)	N8—O6	1.355 (2)
N2—O2	1.345 (2)	N9—C19	1.299 (2)
N3—C3	1.304 (3)	N9—O7	1.342 (2)
N3—O3	1.359 (2)	N10—C20	1.303 (2)
N4—C4	1.296 (3)	N10—O8	1.344 (2)
N4—O4	1.342 (2)	C17—C18	1.466 (3)
C1—C2	1.463 (3)	C17—C21	1.496 (3)
C1—C5	1.498 (3)	C18—C22	1.495 (3)
C2—C6	1.490 (3)	C19—C20	1.461 (3)
C3—C4	1.464 (3)	C19—C23	1.498 (3)
C3—C7	1.496 (3)	C20—C24	1.492 (2)
C4—C8	1.492 (3)	N11—C29	1.486 (3)
N5—C13	1.488 (3)	N11—C25	1.490 (2)
N5—C9	1.490 (3)	C25—C26	1.525 (3)
C9—C10	1.522 (3)	C26—C27	1.487 (5)
C10—C11	1.515 (4)	C27—C28	1.518 (5)
C11—C12	1.497 (4)	C28—C29	1.536 (3)
C12—C13	1.526 (3)	C30A—C31A	1.473 (6)
C14—C15	1.448 (3)	C30A—C32A	1.489 (6)
C14—C16	1.517 (3)	C31A—N12A	1.117 (8)
C15—N6	1.149 (3)	C30B—C31B	1.414 (8)
Co2—N9	1.8840 (15)	C30B—C32B	1.553 (9)
Co2—N10	1.8844 (14)	C31B—N12B	1.144 (10)
N3—Co1—N4	81.54 (7)	N8—Co2—N7	80.92 (7)
N3—Co1—N2	98.00 (7)	N9—Co2—C30A	94.71 (13)
N4—Co1—N2	179.40 (7)	N10—Co2—C30A	85.16 (13)
N3—Co1—N1	177.84 (7)	N8—Co2—C30A	94.94 (13)
N4—Co1—N1	98.65 (7)	N7—Co2—C30A	85.22 (13)
N2—Co1—N1	81.83 (7)	N9—Co2—C30B	83.28 (19)
N3—Co1—C14	90.91 (8)	N10—Co2—C30B	92.99 (18)
N4—Co1—C14	90.62 (8)	N8—Co2—C30B	87.22 (18)
N2—Co1—C14	89.77 (8)	N7—Co2—C30B	96.61 (19)
N1—Co1—C14	86.94 (8)	C30A—Co2—C30B	14.94 (13)
N3—Co1—N5	93.49 (7)	N9—Co2—N11	87.64 (7)
N4—Co1—N5	91.56 (6)	N10—Co2—N11	87.93 (7)
N2—Co1—N5	88.09 (7)	N8—Co2—N11	91.95 (6)
N1—Co1—N5	88.66 (6)	N7—Co2—N11	92.45 (7)
C14—Co1—N5	175.34 (7)	C30A—Co2—N11	172.29 (12)
C1—N1—O1	121.37 (16)	C30B—Co2—N11	170.64 (19)
C1—N1—Co1	116.26 (13)	C17—N7—O5	120.61 (17)
O1—N1—Co1	122.29 (12)	C17—N7—Co2	116.96 (14)
C2—N2—O2	121.07 (16)	O5—N7—Co2	122.24 (13)
C2—N2—Co1	116.03 (13)	C18—N8—O6	120.34 (15)
O2—N2—Co1	122.89 (13)	C18—N8—Co2	116.96 (13)
C3—N3—O3	119.89 (17)	O6—N8—Co2	122.70 (11)
C3—N3—Co1	116.74 (14)	C19—N9—O7	121.24 (15)
O3—N3—Co1	123.33 (13)	C19—N9—Co2	116.36 (13)
C4—N4—O4	120.45 (16)	O7—N9—Co2	122.40 (11)
C4—N4—Co1	116.70 (14)	C20—N10—O8	120.60 (14)
O4—N4—Co1	122.83 (12)	C20—N10—Co2	116.61 (12)
N1—C1—C2	112.98 (16)	O8—N10—Co2	122.77 (12)
N1—C1—C5	123.5 (2)	N7—C17—C18	112.54 (17)
C2—C1—C5	123.5 (2)	N7—C17—C21	123.7 (2)
N2—C2—C1	112.89 (17)	C18—C17—C21	123.8 (2)
N2—C2—C6	122.2 (2)	N8—C18—C17	112.35 (16)
C1—C2—C6	124.9 (2)	N8—C18—C22	124.6 (2)
N3—C3—C4	112.28 (17)	C17—C18—C22	122.99 (18)
N3—C3—C7	122.3 (2)	N9—C19—C20	113.06 (16)
C4—C3—C7	125.4 (2)	N9—C19—C23	123.47 (18)
N4—C4—C3	112.63 (17)	C20—C19—C23	123.47 (17)
N4—C4—C8	123.8 (2)	N10—C20—C19	112.23 (14)
C3—C4—C8	123.5 (2)	N10—C20—C24	124.15 (18)
C13—N5—C9	109.77 (17)	C19—C20—C24	123.61 (17)
C13—N5—Co1	116.03 (13)	C29—N11—C25	109.41 (17)
C9—N5—Co1	116.06 (12)	C29—N11—Co2	115.94 (12)
N5—C9—C10	112.6 (2)	C25—N11—Co2	116.67 (13)
C11—C10—C9	110.9 (2)	N11—C25—C26	111.89 (19)
C12—C11—C10	109.6 (2)	C27—C26—C25	111.9 (2)
C11—C12—C13	111.6 (2)	C26—C27—C28	109.6 (2)
N5—C13—C12	112.6 (2)	C27—C28—C29	111.0 (2)
C15—C14—C16	108.67 (18)	N11—C29—C28	111.0 (2)
C15—C14—Co1	111.55 (13)	C31A—C30A—C32A	111.1 (3)
C16—C14—Co1	116.85 (19)	C31A—C30A—Co2	109.9 (3)
N6—C15—C14	177.3 (2)	C32A—C30A—Co2	117.4 (3)
N9—Co2—N10	81.63 (7)	N12A—C31A—C30A	177.8 (7)
N9—Co2—N8	98.86 (6)	C31B—C30B—C32B	108.0 (5)
N10—Co2—N8	179.49 (7)	C31B—C30B—Co2	113.4 (5)
N9—Co2—N7	179.76 (7)	C32B—C30B—Co2	113.7 (4)
N10—Co2—N7	98.59 (7)	N12B—C31B—C30B	177.2 (10)

(3-neutron) '[(R,S)-1-cyanoethyl](piperidine)bis(dimethylglyoximato)cobalt(III) irradiated'

Crystal data

C16H28CoDN6O4	Dx = 0.730 Mg m^−3
Mr = 429.38	Neutron radiation, λ = 1.06000 Å
Orthorhombic, P212121	Cell parameters from 512 (determined by X-ray) reflections
a = 11.4039 (2) Å	θ = 1.9 (X-ray, MoKα)–35.0 (X-ray, MoKα)°
b = 11.7354 (1) Å	µ = 0.24 mm^−1
c = 30.7446 (2) Å	T = 293 K
V = 4114.53 (8) Å^3	Plate, dark red
Z = 8	3.0 × 3.0 × 1.0 mm
F(000) = 72

Data collection

BIX-I diffractometer	2124 reflections with I > 2σ(I)
Radiation source: JRR-3M atomic reactor	Rint = 0.063
Bent Si crystal monochromator	θmax = 43.6°, θmin = 2.0°
0.2deg ω step scan	h = −12→11
2928 measured reflections	k = −3→12
2137 independent reflections	l = −28→32

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full with fixed elements per cycle	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.104	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.268	w = 1/[σ^2(Fo^2) + (0.2309P)^2 + 0.6072P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.056
2137 reflections	Δρmax = 0.11 e Å^−3
805 parameters	Δρmin = −0.08 e Å^−3
11 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (10)

Special details

Experimental. The crystal was obtained by slow evaporation from methanol/water.

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	0.6455	0.5133	0.8778	0.0539 (14)*
N1	0.6899	0.6395	0.8435	0.0538 (5)
N2	0.5133	0.5174	0.8409	0.0605 (6)
N3	0.6039	0.3840	0.9104	0.0573 (6)
N4	0.7764	0.5087	0.9152	0.0642 (6)
O1	0.7934	0.6939	0.8490	0.0796 (14)
HO1	0.8365 (5)	0.6497 (6)	0.8778 (2)	0.093 (2)
O2	0.4227	0.4446	0.8449	0.0935 (16)
O3	0.5043	0.3231	0.9033	0.0880 (14)
HO3	0.4726 (5)	0.3549 (4)	0.87828 (17)	0.0676 (15)
O4	0.8672	0.5810	0.9115	0.0777 (11)
C1	0.6181	0.6684	0.8129	0.0641 (9)
C2	0.5130	0.5969	0.8115	0.0708 (10)
C3	0.6738	0.3558	0.9422	0.0699 (10)
C4	0.7766	0.4300	0.9446	0.0710 (10)
C5	0.6413	0.7634	0.7815	0.0806 (11)
H5A	0.7204 (8)	0.7763 (7)	0.7764 (3)	0.157 (3)
H5B	0.6074 (7)	0.8418 (9)	0.7938 (2)	0.107 (3)
H5C	0.6044 (11)	0.7534 (13)	0.7521 (2)	0.193 (5)
C6	0.4141	0.6116	0.7803	0.128 (2)
H6A	0.3627 (6)	0.5371 (5)	0.7790 (3)	0.168 (3)
H6B	0.4525 (8)	0.6394 (11)	0.7482 (3)	0.164 (4)
H6C	0.3571 (11)	0.6796 (10)	0.7865 (2)	0.129 (4)
C7	0.6473	0.2593	0.9724	0.0829 (11)
H7A	0.5861 (12)	0.2002 (12)	0.9547 (3)	0.193 (5)
H7B	0.6114 (10)	0.2822 (6)	0.9985 (2)	0.139 (3)
H7C	0.7209 (9)	0.1908 (7)	0.9689 (3)	0.181 (3)
C8	0.8743	0.4126	0.9763	0.1033 (14)
H8A	0.9093 (7)	0.3307 (5)	0.9708 (4)	0.211 (7)
H8B	0.8524 (9)	0.3691 (7)	1.00528 (19)	0.229 (4)
H8C	0.9141 (11)	0.4751 (7)	0.9747 (4)	0.187 (4)
N5	0.5569	0.6259	0.9196	0.0645 (6)
HN5	0.5039 (4)	0.6781 (5)	0.8998 (2)	0.111 (3)
C9	0.6321	0.7024	0.9464	0.0960 (10)
H9A	0.6854 (6)	0.6521 (5)	0.9704 (2)	0.089 (2)
H9B	0.6848 (8)	0.7504 (5)	0.9251 (2)	0.095 (2)
C10	0.5618	0.7935	0.9700	0.0852 (11)
H10A	0.5277 (6)	0.8461 (5)	0.9428 (3)	0.092 (2)
H10B	0.6275 (6)	0.8397 (4)	0.9910 (3)	0.138 (3)
C11	0.4681	0.7401	0.9985	0.0875 (12)
H11A	0.5227 (7)	0.6969 (7)	1.0213 (4)	0.162 (4)
H11B	0.4055 (5)	0.7905 (8)	1.0152 (2)	0.114 (3)
C12	0.3919	0.6642	0.9714	0.1045 (15)
H12A	0.3456 (7)	0.7256 (5)	0.9550 (3)	0.137 (3)
H12B	0.3302 (6)	0.6228 (7)	0.9891 (2)	0.113 (2)
C13	0.4638	0.5746	0.9473	0.0700 (10)
H13A	0.4165 (7)	0.5235 (9)	0.9352 (4)	0.142 (4)
H13B	0.5203 (7)	0.5247 (7)	0.9683 (2)	0.110 (2)
C14	0.7320	0.4132	0.8332	0.0655 (10)
D14	0.7748 (5)	0.4737 (4)	0.81373 (15)	0.1083 (16)
C15	0.8241	0.3469	0.8534	0.1043 (15)
C16	0.6572	0.3344	0.8056	0.0967 (12)
H16A	0.6122 (6)	0.3454 (6)	0.78379 (18)	0.1500 (19)
H16B	0.6029 (9)	0.2874 (5)	0.8261 (3)	0.117 (3)
H16C	0.7236 (5)	0.2755 (5)	0.7863 (2)	0.110 (2)
N6	0.8942	0.2906	0.8695	0.1138 (11)
Co2	0.1510	1.0070	0.8504	0.0450 (12)*
N7	0.1277	0.8921	0.8081	0.0638 (6)
N8	0.1577	0.8778	0.8869	0.0586 (6)
N9	0.1744	1.1209	0.8926	0.0690 (7)
N10	0.1437	1.1351	0.8135	0.0653 (6)
O5	0.1124	0.9164	0.7656	0.0697 (11)
HO5	0.1093 (7)	1.0072 (6)	0.7633 (2)	0.096 (2)
O6	0.1827	0.8847	0.9299	0.0653 (11)
O7	0.1943	1.0964	0.9344	0.0874 (14)
HO7	0.2071 (6)	0.9898 (5)	0.93389 (18)	0.0854 (17)
O8	0.1288	1.1267	0.7703	0.0649 (10)
C17	0.1184	0.7889	0.8219	0.0684 (9)
C18	0.1381	0.7796	0.8689	0.0624 (9)
C19	0.1710	1.2256	0.8790	0.0675 (10)
C20	0.1514	1.2345	0.8322	0.0766 (10)
C21	0.0873	0.6900	0.7935	0.0990 (14)
H21A	0.1547 (6)	0.6299 (3)	0.7895 (2)	0.145 (4)
H21B	0.0575 (12)	0.6975 (5)	0.76133 (16)	0.272 (12)
H21C	0.0361 (7)	0.6401 (6)	0.8152 (2)	0.273 (4)
C22	0.1406	0.6684	0.8925	0.1007 (15)
H22A	0.1560 (8)	0.6835 (3)	0.92827 (14)	0.102 (2)
H22B	0.0763 (9)	0.6215 (15)	0.8844 (2)	0.210 (5)
H22C	0.2130 (7)	0.6263 (6)	0.8814 (3)	0.114 (3)
C23	0.1874	1.3267	0.9081	0.0924 (14)
H23A	0.2469 (4)	1.3885 (4)	0.8966 (2)	0.1143 (18)
H23B	0.2062 (9)	1.3136 (6)	0.9372 (2)	0.131 (3)
H23C	0.1073 (11)	1.3721 (10)	0.9189 (3)	0.243 (4)
C24	0.1412	1.3453	0.8086	0.0725 (10)
H24A	0.120 (2)	1.3488 (6)	0.77827 (17)	0.342 (12)
H24B	0.2185 (9)	1.3824 (5)	0.8106 (3)	0.170 (3)
H24C	0.0800 (6)	1.4044 (6)	0.8249 (5)	0.181 (5)
N11	−0.0293	1.0259	0.8608	0.0708 (7)
HN11	−0.0366 (4)	1.1137 (3)	0.86481 (19)	0.0596 (15)
C25	−0.1079	0.9925	0.8242	0.0779 (11)
H25A	−0.1121 (8)	0.9028 (4)	0.82017 (17)	0.127 (3)
H25B	−0.0683 (5)	1.0157 (7)	0.79440 (13)	0.113 (2)
C26	−0.2339	1.0314	0.8319	0.0989 (14)
H26A	−0.2311 (7)	1.1046 (7)	0.8369 (4)	0.179 (4)
H26B	−0.2874 (7)	1.0236 (8)	0.8033 (3)	0.118 (3)
C27	−0.2819	0.9863	0.8734	0.1127 (16)
H27A	−0.3669 (7)	1.0228 (12)	0.8750 (4)	0.200 (4)
H27B	−0.2953 (9)	0.8860 (7)	0.8694 (6)	0.239 (6)
C28	−0.2011	1.0186	0.9107	0.1254 (19)
H28A	−0.2301 (6)	0.9806 (15)	0.9410 (3)	0.274 (6)
H28B	−0.1872 (12)	1.1063 (4)	0.91385 (19)	0.168 (5)
C29	−0.0753	0.9777	0.9021	0.0801 (11)
H29A	−0.0091 (8)	0.9965 (7)	0.9289 (3)	0.105 (2)*
H29B	−0.0691 (9)	0.8921 (5)	0.8993 (3)	0.161 (3)
C30A	0.3238	0.9991	0.8323	0.0304 (8)*	0.497 (3)
D30A	0.3142 (7)	0.9954 (6)	0.7964 (2)	0.0741 (17)*	0.497 (3)
C31A	0.3757	0.8911	0.8473	0.0795 (18)*	0.497 (3)
C32A	0.3998	1.0977	0.8438	0.0518 (12)*	0.497 (3)
H32A	0.3584 (10)	1.1696 (9)	0.8309 (3)	0.061 (2)*	0.497 (3)
H32B	0.4742 (11)	1.1261 (10)	0.8436 (4)	0.067 (3)*	0.497 (3)
H32C	0.3990 (7)	1.0978 (6)	0.8774 (3)	0.0355 (16)*	0.497 (3)
N12A	0.4183	0.8112	0.8591	0.157 (3)*	0.497 (3)
C30B	0.3336	1.0032	0.8494	0.0602 (13)*	0.503 (3)
D30B	0.3764 (6)	1.0741 (5)	0.8767 (2)	0.0633 (15)*	0.503 (3)
C31B	0.3809	0.8942	0.8581	0.0571 (13)*	0.503 (3)
C32B	0.3875	1.0465	0.8060	0.180 (6)*	0.503 (3)
H32D	0.3520 (7)	1.1333 (9)	0.79840 (18)	0.151 (8)*	0.503 (3)
H32E	0.3640 (7)	0.9862 (7)	0.7791 (3)	0.154*	0.503 (3)
H32F	0.4853 (9)	1.0511 (8)	0.80922 (11)	0.068 (3)*	0.503 (3)
N12B	0.4180	0.8048	0.8635	0.0636 (11)*	0.503 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0362 (9)	0.0580 (9)	0.0670 (11)	0.0082 (7)	−0.0022 (9)	0.0059 (8)
N2	0.0503 (11)	0.0689 (10)	0.0625 (10)	−0.0074 (8)	−0.0150 (9)	0.0193 (9)
N3	0.0573 (10)	0.0535 (9)	0.0610 (11)	−0.0122 (8)	−0.0024 (10)	−0.0106 (8)
N4	0.0244 (8)	0.0827 (12)	0.0854 (13)	0.0100 (8)	−0.0086 (10)	0.0117 (11)
O1	0.0356 (17)	0.080 (2)	0.123 (3)	0.0128 (15)	0.0045 (19)	−0.003 (2)
HO1	0.045 (3)	0.149 (4)	0.084 (3)	−0.055 (2)	−0.008 (3)	0.027 (3)
O2	0.071 (3)	0.097 (3)	0.113 (3)	−0.013 (2)	0.003 (3)	0.025 (2)
O3	0.0537 (16)	0.0311 (13)	0.179 (4)	−0.0328 (10)	0.007 (2)	0.0121 (18)
HO3	0.059 (3)	0.066 (3)	0.077 (3)	−0.027 (2)	0.030 (2)	−0.031 (2)
O4	0.0471 (16)	0.133 (2)	0.0526 (17)	0.0508 (13)	−0.0101 (16)	−0.0174 (17)
C1	0.0315 (13)	0.0922 (18)	0.0685 (16)	−0.0017 (13)	0.0032 (14)	0.0140 (15)
C2	0.0393 (15)	0.097 (2)	0.0764 (18)	0.0078 (14)	−0.0067 (15)	−0.0093 (16)
C3	0.0621 (18)	0.0831 (18)	0.0644 (16)	0.0099 (15)	0.0028 (16)	0.0081 (15)
C4	0.0638 (17)	0.0887 (17)	0.0605 (16)	0.0273 (13)	0.0042 (15)	−0.0187 (14)
C5	0.087 (2)	0.0721 (17)	0.0830 (18)	−0.0151 (16)	−0.0326 (18)	0.0251 (15)
H5A	0.082 (5)	0.170 (5)	0.219 (6)	0.015 (4)	0.039 (5)	0.140 (3)
H5B	0.071 (4)	0.166 (7)	0.085 (4)	0.015 (5)	0.038 (4)	0.006 (4)
H5C	0.187 (8)	0.328 (13)	0.064 (3)	0.036 (10)	−0.082 (4)	−0.081 (5)
C6	0.122 (4)	0.173 (4)	0.088 (2)	0.042 (3)	−0.009 (3)	0.027 (3)
H6A	0.106 (5)	0.164 (6)	0.234 (7)	−0.036 (5)	−0.121 (4)	0.096 (5)
H6B	0.126 (6)	0.287 (9)	0.078 (4)	−0.118 (5)	−0.032 (4)	0.051 (5)
H6C	0.156 (8)	0.179 (8)	0.053 (3)	−0.006 (8)	0.019 (5)	0.000 (4)
C7	0.0917 (19)	0.0436 (13)	0.113 (2)	0.0377 (12)	−0.012 (2)	−0.0075 (14)
H7A	0.175 (9)	0.303 (11)	0.100 (4)	0.037 (8)	0.045 (5)	−0.101 (5)
H7B	0.172 (7)	0.122 (4)	0.124 (4)	0.033 (5)	−0.033 (5)	0.086 (3)
H7C	0.223 (6)	0.168 (4)	0.151 (5)	0.144 (3)	0.029 (5)	0.094 (3)
C8	0.0366 (15)	0.196 (3)	0.078 (2)	0.0475 (18)	0.0043 (18)	0.002 (2)
H8A	0.102 (6)	0.39 (2)	0.142 (7)	0.074 (9)	−0.080 (5)	−0.032 (10)
H8B	0.249 (7)	0.281 (7)	0.155 (8)	0.210 (4)	0.048 (7)	0.079 (6)
H8C	0.201 (8)	0.097 (4)	0.261 (8)	−0.076 (4)	−0.136 (6)	0.101 (4)
N5	0.0517 (10)	0.0580 (10)	0.0837 (13)	0.0034 (8)	−0.0082 (11)	0.0137 (10)
HN5	0.021 (2)	0.117 (5)	0.196 (7)	−0.006 (3)	−0.009 (4)	−0.047 (5)
C9	0.0510 (15)	0.1311 (19)	0.1058 (18)	0.0384 (14)	−0.0396 (14)	−0.0784 (13)
H9A	0.103 (4)	0.041 (2)	0.124 (4)	0.005 (3)	−0.051 (4)	0.016 (3)
H9B	0.130 (5)	0.053 (3)	0.100 (4)	−0.036 (3)	0.004 (4)	−0.020 (3)
C10	0.0797 (19)	0.112 (2)	0.0636 (17)	0.0372 (16)	0.0197 (17)	−0.0142 (16)
H10A	0.080 (3)	0.053 (2)	0.144 (5)	0.031 (2)	0.026 (4)	0.030 (3)
H10B	0.113 (4)	0.0204 (18)	0.280 (7)	0.013 (2)	0.120 (4)	0.042 (3)
C11	0.102 (2)	0.0666 (18)	0.094 (2)	0.0186 (17)	0.037 (2)	0.0071 (16)
H11A	0.114 (4)	0.107 (4)	0.265 (9)	0.056 (3)	−0.100 (4)	0.018 (5)
H11B	0.073 (3)	0.180 (6)	0.087 (3)	0.044 (3)	0.078 (2)	0.031 (4)
C12	0.0421 (15)	0.197 (4)	0.0744 (19)	0.034 (2)	0.0323 (16)	0.025 (2)
H12A	0.164 (5)	0.066 (3)	0.182 (6)	0.058 (3)	0.085 (4)	−0.019 (3)
H12B	0.077 (3)	0.147 (4)	0.115 (4)	0.066 (3)	0.071 (3)	0.058 (3)
C13	0.0411 (15)	0.0570 (15)	0.112 (2)	−0.0019 (12)	−0.0030 (17)	0.0096 (16)
H13A	0.061 (4)	0.155 (6)	0.210 (9)	−0.032 (4)	0.034 (5)	0.048 (6)
H13B	0.101 (4)	0.161 (5)	0.068 (3)	0.059 (3)	−0.032 (3)	0.025 (3)
C14	0.0465 (15)	0.0843 (19)	0.0657 (17)	−0.0082 (13)	−0.0054 (15)	0.0016 (14)
D14	0.108 (3)	0.103 (2)	0.114 (3)	0.006 (2)	−0.005 (3)	−0.045 (2)
C15	0.093 (3)	0.091 (2)	0.129 (3)	−0.013 (2)	0.015 (3)	−0.024 (2)
C16	0.0703 (18)	0.0672 (16)	0.153 (3)	0.0329 (13)	−0.043 (2)	−0.0420 (17)
H16A	0.121 (4)	0.248 (4)	0.081 (3)	−0.127 (3)	−0.038 (3)	0.117 (2)
H16B	0.180 (7)	0.062 (3)	0.110 (5)	0.050 (4)	0.009 (5)	−0.030 (3)
H16C	0.076 (2)	0.098 (3)	0.156 (5)	−0.0596 (18)	−0.063 (3)	−0.023 (3)
N6	0.0830 (16)	0.1229 (18)	0.136 (2)	0.0488 (14)	−0.0171 (18)	−0.0374 (17)
N7	0.0674 (13)	0.0660 (11)	0.0582 (11)	−0.0059 (10)	−0.0070 (11)	−0.0191 (8)
N8	0.0233 (8)	0.0573 (9)	0.0954 (13)	0.0110 (7)	0.0076 (9)	0.0142 (9)
N9	0.0728 (13)	0.0732 (12)	0.0609 (11)	0.0138 (11)	−0.0174 (11)	−0.0168 (9)
N10	0.0435 (10)	0.0851 (12)	0.0673 (11)	0.0135 (9)	−0.0114 (10)	0.0114 (10)
O5	0.065 (2)	0.079 (2)	0.0658 (19)	−0.0152 (16)	−0.0122 (18)	0.0049 (16)
HO5	0.095 (4)	0.098 (3)	0.096 (3)	0.030 (3)	−0.022 (3)	−0.058 (2)
O6	0.094 (2)	0.0772 (19)	0.0249 (13)	−0.0035 (19)	−0.0182 (15)	0.0136 (12)
O7	0.085 (3)	0.100 (3)	0.078 (2)	−0.008 (2)	−0.034 (2)	0.009 (2)
HO7	0.112 (3)	0.069 (3)	0.075 (3)	0.054 (2)	−0.045 (3)	−0.020 (2)
O8	0.074 (2)	0.0660 (17)	0.0549 (17)	0.0243 (16)	−0.0089 (16)	0.0054 (14)
C17	0.0584 (16)	0.0424 (12)	0.104 (2)	0.0040 (12)	−0.0181 (16)	−0.0243 (12)
C18	0.0558 (15)	0.0542 (13)	0.0771 (17)	−0.0034 (11)	0.0186 (14)	0.0140 (13)
C19	0.0605 (16)	0.0519 (14)	0.090 (2)	−0.0192 (12)	−0.0008 (16)	−0.0084 (13)
C20	0.115 (2)	0.0468 (13)	0.0680 (16)	0.0271 (14)	−0.0052 (19)	0.0164 (12)
C21	0.081 (2)	0.122 (3)	0.094 (3)	−0.0413 (19)	−0.021 (2)	0.000 (2)
H21A	0.250 (9)	0.020 (2)	0.164 (5)	−0.032 (4)	0.088 (6)	−0.052 (2)
H21B	0.68 (4)	0.018 (2)	0.113 (6)	0.026 (8)	0.099 (11)	0.003 (3)
H21C	0.586 (11)	0.128 (4)	0.104 (5)	−0.232 (4)	0.096 (6)	0.004 (3)
C22	0.0461 (18)	0.110 (3)	0.146 (3)	0.0136 (18)	0.005 (2)	0.017 (3)
H22A	0.235 (6)	0.0188 (18)	0.051 (2)	−0.037 (3)	0.075 (3)	−0.0031 (16)
H22B	0.142 (5)	0.390 (15)	0.098 (4)	−0.090 (9)	−0.104 (3)	0.105 (6)
H22C	0.073 (4)	0.063 (3)	0.206 (8)	−0.009 (3)	0.042 (5)	−0.020 (4)
C23	0.096 (3)	0.081 (2)	0.100 (2)	0.002 (2)	0.023 (2)	−0.0154 (19)
H23A	0.057 (3)	0.118 (3)	0.168 (4)	−0.032 (2)	0.023 (3)	−0.120 (2)
H23B	0.226 (7)	0.082 (3)	0.083 (4)	−0.092 (3)	−0.033 (5)	0.022 (3)
H23C	0.130 (7)	0.421 (8)	0.179 (4)	−0.033 (7)	0.052 (5)	−0.239 (3)
C24	0.0593 (17)	0.0652 (16)	0.093 (2)	0.0114 (14)	0.0031 (18)	0.0120 (15)
H24A	0.92 (4)	0.100 (4)	0.009 (2)	0.139 (12)	−0.039 (8)	−0.016 (3)
H24B	0.205 (6)	0.050 (3)	0.256 (7)	0.035 (3)	−0.101 (5)	0.069 (3)
H24C	0.074 (3)	0.079 (4)	0.389 (13)	0.041 (2)	0.111 (5)	−0.001 (6)
N11	0.0319 (10)	0.1082 (15)	0.0722 (13)	−0.0098 (10)	−0.0103 (10)	0.0047 (12)
HN11	0.053 (3)	0.0284 (18)	0.097 (3)	−0.0035 (18)	0.011 (3)	−0.023 (2)
C25	0.0486 (16)	0.095 (2)	0.090 (2)	−0.0167 (15)	−0.0292 (16)	0.0070 (17)
H25A	0.143 (6)	0.215 (7)	0.024 (2)	0.084 (5)	−0.002 (3)	0.012 (3)
H25B	0.080 (3)	0.205 (5)	0.055 (2)	−0.054 (3)	−0.045 (2)	−0.039 (3)
C26	0.0528 (15)	0.0344 (13)	0.209 (4)	−0.0112 (10)	−0.052 (2)	0.0229 (18)
H26A	0.085 (4)	0.129 (4)	0.322 (11)	0.047 (3)	−0.056 (5)	0.093 (5)
H26B	0.089 (4)	0.141 (6)	0.124 (4)	0.018 (4)	−0.073 (3)	−0.024 (4)
C27	0.069 (2)	0.094 (2)	0.175 (4)	0.0259 (17)	−0.040 (2)	0.018 (3)
H27A	0.072 (3)	0.278 (9)	0.251 (9)	−0.104 (4)	0.103 (5)	−0.094 (8)
H27B	0.185 (6)	0.054 (4)	0.476 (16)	−0.055 (3)	0.175 (7)	0.006 (6)
C28	0.097 (3)	0.190 (4)	0.089 (2)	0.023 (3)	0.007 (3)	0.049 (3)
H28A	0.059 (3)	0.614 (17)	0.150 (5)	0.160 (6)	0.080 (4)	0.193 (7)
H28B	0.282 (14)	0.182 (7)	0.040 (3)	−0.004 (8)	−0.037 (5)	−0.059 (3)
C29	0.0524 (18)	0.126 (2)	0.0616 (16)	0.0000 (17)	0.0048 (15)	0.0305 (17)
H29B	0.140 (6)	0.049 (2)	0.295 (8)	0.025 (3)	0.068 (6)	0.108 (3)

Geometric parameters (Å, º)

Co1—N3	1.8794	Co2—N7	1.8920
Co1—N4	1.8849	Co2—C30A	2.0498
Co1—N1	1.8872	Co2—C30B	2.0829
Co1—N2	1.8873	Co2—N11	2.0933
Co1—C14	2.0575	Co2—D30A	2.497 (7)
Co1—N5	2.1021	Co2—D30B	2.808 (7)
Co1—D14	2.504 (5)	N7—C17	1.2878
N1—C1	1.2924	N7—O5	1.3489
N1—O1	1.3526	N8—C18	1.2978
N2—C2	1.2990	N8—O6	1.3548
N2—O2	1.3466	N9—C19	1.2983
N3—C3	1.3041	N9—O7	1.3374
N3—O3	1.3596	N10—C20	1.3030
N4—C4	1.2918	N10—O8	1.3426
N4—O4	1.3438	C17—C18	1.4664
C1—C2	1.4639	C17—C21	1.4954
C1—C5	1.4983	C18—C22	1.4928
C2—C6	1.4907	C19—C20	1.4598
C3—C4	1.4617	C19—C23	1.4977
C3—C7	1.4950	C20—C24	1.4940
C4—C8	1.4949	N11—C29	1.4853
N5—C13	1.4884	N11—C25	1.4911
N5—C9	1.4896	C25—C26	1.5261
C9—C10	1.5207	C26—C27	1.4855
C10—C11	1.5175	C27—C28	1.5190
C11—C12	1.4975	C28—C29	1.5364
C12—C13	1.5255	C30A—D30A	1.109 (7)
C14—D14	1.050 (5)	C30A—C31A	1.4727
C14—C15	1.4472	C30A—C32A	1.4882
C14—C16	1.5175	C31A—N12A	1.1166
C15—N6	1.1492	C30B—D30B	1.279 (6)
Co2—N9	1.8819	C30B—C31B	1.4138
Co2—N10	1.8852	C30B—C32B	1.5544
Co2—N8	1.8879	C31B—N12B	1.1433
N3—Co1—N4	81.452 (1)	N8—Co2—C30B	87.2
N3—Co1—N1	177.839 (1)	N7—Co2—C30B	96.6
N4—Co1—N1	98.682 (1)	C30A—Co2—C30B	15.0
N3—Co1—N2	98.019 (1)	N9—Co2—N11	87.6
N4—Co1—N2	179.327 (1)	N10—Co2—N11	87.937 (1)
N1—Co1—N2	81.863 (1)	N8—Co2—N11	91.948 (1)
N3—Co1—C14	90.878 (1)	N7—Co2—N11	92.4
N4—Co1—C14	90.604 (1)	C30A—Co2—N11	172.3
N1—Co1—C14	86.964 (1)	C30B—Co2—N11	170.7
N2—Co1—C14	89.820 (1)	N9—Co2—D30A	113.03 (17)
N3—Co1—N5	93.457 (1)	N10—Co2—D30A	71.13 (17)
N4—Co1—N5	91.473 (1)	N8—Co2—D30A	108.72 (17)
N1—Co1—N5	88.7	N7—Co2—D30A	66.99 (17)
N2—Co1—N5	88.141 (1)	C30A—Co2—D30A	25.92 (17)
C14—Co1—N5	175.4	C30B—Co2—D30A	40.88 (17)
N3—Co1—D14	114.73 (11)	N11—Co2—D30A	147.10 (17)
N4—Co1—D14	90.46 (12)	N9—Co2—D30B	58.15 (13)
N1—Co1—D14	63.13 (11)	N10—Co2—D30B	89.44 (13)
N2—Co1—D14	90.14 (12)	N8—Co2—D30B	90.98 (12)
C14—Co1—D14	24.15 (11)	N7—Co2—D30B	121.77 (13)
N5—Co1—D14	151.71 (11)	C30A—Co2—D30B	37.88 (13)
C1—N1—O1	121.321 (1)	C30B—Co2—D30B	25.17 (13)
C1—N1—Co1	116.281 (1)	N11—Co2—D30B	145.68 (13)
O1—N1—Co1	122.3	D30A—Co2—D30B	61.6 (2)
C2—N2—O2	121.152 (1)	C17—N7—O5	120.501 (1)
C2—N2—Co1	116.0	C17—N7—Co2	117.1
O2—N2—Co1	122.8	O5—N7—Co2	122.237 (1)
C3—N3—O3	119.841 (1)	C18—N8—O6	120.331 (1)
C3—N3—Co1	116.771 (1)	C18—N8—Co2	116.946 (2)
O3—N3—Co1	123.341 (1)	O6—N8—Co2	122.720 (1)
C4—N4—O4	120.629 (1)	C19—N9—O7	121.2
C4—N4—Co1	116.629 (1)	C19—N9—Co2	116.482 (1)
O4—N4—Co1	122.725 (1)	O7—N9—Co2	122.3
N1—C1—C2	112.930 (1)	C20—N10—O8	120.7
N1—C1—C5	123.538 (1)	C20—N10—Co2	116.4
C2—C1—C5	123.518 (1)	O8—N10—Co2	122.8
N2—C2—C1	112.896 (1)	N7—C17—C18	112.5
N2—C2—C6	122.2	N7—C17—C21	123.8
C1—C2—C6	124.895 (1)	C18—C17—C21	123.7
N3—C3—C4	112.101 (2)	N8—C18—C17	112.327 (1)
N3—C3—C7	122.3	N8—C18—C22	124.474 (2)
C4—C3—C7	125.611 (1)	C17—C18—C22	123.141 (1)
N4—C4—C3	112.942 (1)	N9—C19—C20	112.9
N4—C4—C8	123.7	N9—C19—C23	123.606 (1)
C3—C4—C8	123.299 (1)	C20—C19—C23	123.5
C13—N5—C9	109.768 (1)	N10—C20—C19	112.4
C13—N5—Co1	115.990 (1)	N10—C20—C24	124.0
C9—N5—Co1	116.103 (2)	C19—C20—C24	123.5
N5—C9—C10	112.583 (2)	C29—N11—C25	109.449 (2)
C11—C10—C9	110.888 (1)	C29—N11—Co2	115.887 (1)
C12—C11—C10	109.439 (1)	C25—N11—Co2	116.573 (1)
C11—C12—C13	111.622 (2)	N11—C25—C26	111.723 (2)
N5—C13—C12	112.466 (1)	C27—C26—C25	111.915 (1)
D14—C14—C15	105.7 (3)	C26—C27—C28	109.646 (1)
D14—C14—C16	110.8 (3)	C27—C28—C29	111.013 (1)
C15—C14—C16	108.677 (1)	N11—C29—C28	110.935 (1)
D14—C14—Co1	102.5 (3)	D30A—C30A—C31A	108.5 (4)
C15—C14—Co1	111.651 (2)	D30A—C30A—C32A	108.9 (4)
C16—C14—Co1	116.821 (1)	C31A—C30A—C32A	111.143 (1)
C14—D14—Co1	53.3 (2)	D30A—C30A—Co2	100.2 (4)
N6—C15—C14	177.3	C31A—C30A—Co2	109.887 (1)
N9—Co2—N10	81.644 (1)	C32A—C30A—Co2	117.394 (1)
N9—Co2—N8	98.916 (1)	C30A—D30A—Co2	53.9 (3)
N10—Co2—N8	179.424 (1)	N12A—C31A—C30A	177.7
N9—Co2—N7	179.8	D30B—C30B—C31B	108.6 (3)
N10—Co2—N7	98.5	D30B—C30B—C32B	101.5 (3)
N8—Co2—N7	80.899 (1)	C31B—C30B—C32B	107.900 (1)
N9—Co2—C30A	94.8	D30B—C30B—Co2	111.0 (3)
N10—Co2—C30A	85.1	C31B—C30B—Co2	113.451 (1)
N8—Co2—C30A	94.945 (1)	C32B—C30B—Co2	113.6
N7—Co2—C30A	85.2	C30B—D30B—Co2	43.8 (2)
N9—Co2—C30B	83.3	N12B—C31B—C30B	177.3
N10—Co2—C30B	93.0