(2-Carbamoyl­ethyl)­bis­(di­methyl­glyoximato-N,N')[(R)-1-(1-naphthyl)­ethyl­amine]­cobalt(III) ethanol solvate and bis­(di­methyl­glyoximato-N,N')[2-(N-methyl­carbamoyl)­ethyl][methyl (S)-phenyl­alaninate-N]­cobalt(III)

The 2-carbamoyl­ethyl and 2-(methyl­carbamoyl)­ethyl groups in the title cobaloxime complexes, [Co(C₄H₇N₂O₂)₂(C₃H₆­NO)(C₁₂H₁₃N)]·C₂H₆O and [Co(C₄H₇N₂O₂)₂(C₄H₈NO)(C₁₀H₁₃NO₂)], were isomerized to 1-carbamoyl­ethyl and 1-(methyl­carbamoyl)­ethyl groups, respectively, on exposure to visible light in the solid state. Although both the crystal structures and the intermolecular hydrogen bonds are different in the two crystals, similar reaction rates were observed.

Computing details

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

(I) (2-Carbamoylethyl)bis(dimethylglyoximato) [(R)-1-(1-naphthyl)ethylamine]cobalt(III)

Crystal data

[Co(C4H7N2O2)2(C3H6NO)(C12H13N)]·C2H6O	F(000) = 612
Mr = 578.55	Dx = 1.331 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.852 (3) Å	Cell parameters from 25 reflections
b = 15.962 (5) Å	θ = 12.5–15.0°
c = 11.951 (4) Å	µ = 0.64 mm^−1
β = 105.48 (3)°	T = 298 K
V = 1443.6 (9) Å^3	Prismatic, red
Z = 2	0.50 × 0.50 × 0.10 mm

Data collection

RIGAKU AFC5 diffractometer	3097 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 1.8°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→20
Tmin = 0.740, Tmax = 0.939	l = −15→14
3442 measured reflections	3 standard reflections every 100 reflections
3442 independent reflections	intensity decay: none

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.124	Calculated w = 1/[σ^2(Fo^2) + (0.0887P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
3442 reflections	Δρmax = 1.05 e Å^−3
356 parameters	Δρmin = −0.39 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: 0.00 (2)

Special details

Experimental. (2-Carbamoylethyl)bis(dimethylglyoximato) [(R)-1-(1-naphthyl)ethylamine]cobalt(III) and bis(dimethylglyoximato) [2-(methylcarbamoyl)ethyl][methyl (S)-phenylalaninate]cobalt(III)

The preparation of the series of N-substituted cobaloxime complexes was basically carried out according to the literature methods with minor change·(Ohgo et al., 1996) The crystal was obtained by slow evaporation from ethanol/hexane.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Co1	0.06936 (6)	0.00589 (3)	−0.11717 (4)	0.03043 (14)
O1	−0.2735 (4)	−0.0596 (2)	−0.1403 (3)	0.0499 (8)
O2	0.3880 (5)	−0.0320 (3)	0.0580 (4)	0.0701 (11)
H02	0.3975	0.0099	−0.0031	0.084*
O3	0.4110 (4)	0.0719 (3)	−0.0926 (4)	0.0627 (9)
O4	−0.2501 (4)	0.0446 (2)	−0.2911 (3)	0.0482 (7)
H04	−0.2596	0.0025	−0.2304	0.058*
O5	−0.0752 (5)	0.2455 (2)	0.0912 (4)	0.0577 (9)
N1	−0.1060 (5)	−0.0585 (2)	−0.0753 (3)	0.0373 (7)
N2	0.2112 (5)	−0.0447 (2)	0.0186 (3)	0.0447 (8)
N3	0.2429 (5)	0.0745 (2)	−0.1539 (3)	0.0427 (8)
N4	−0.0752 (4)	0.0600 (2)	−0.2484 (3)	0.0364 (7)
N5	−0.3610 (6)	0.2083 (3)	0.0375 (4)	0.0614 (12)
H05A	−0.3902	0.2478	0.0777	0.074*
H05B	−0.4404	0.1748	−0.0020	0.074*
N6	0.1271 (5)	−0.0958 (2)	−0.2113 (3)	0.0356 (7)
H06A	0.2426	−0.0924	−0.2087	0.043*
H06B	0.1134	−0.1426	−0.1727	0.043*
C1	−0.0565 (7)	−0.1014 (3)	0.0196 (4)	0.0469 (10)
C2	0.1337 (7)	−0.0943 (3)	0.0752 (4)	0.0499 (11)
C3	0.1887 (7)	0.1245 (3)	−0.2408 (5)	0.0503 (11)
C4	0.0005 (7)	0.1161 (3)	−0.2965 (4)	0.0480 (11)
C5	−0.1805 (10)	−0.1532 (4)	0.0661 (6)	0.0714 (17)
H5A	−0.1309	−0.1622	0.1478	0.107*
H5B	−0.1988	−0.2062	0.0268	0.107*
H5C	−0.2914	−0.1245	0.0537	0.107*
C6	0.2278 (10)	−0.1395 (5)	0.1829 (5)	0.0798 (19)
H6A	0.1895	−0.1969	0.1779	0.120*
H6B	0.2016	−0.1134	0.2488	0.120*
H6C	0.3528	−0.1375	0.1916	0.120*
C7	0.3112 (10)	0.1829 (4)	−0.2808 (7)	0.081 (2)
H7A	0.2804	0.2398	−0.2693	0.121*
H7B	0.3006	0.1736	−0.3618	0.121*
H7C	0.4308	0.1724	−0.2369	0.121*
C8	−0.1017 (10)	0.1670 (4)	−0.3989 (5)	0.0737 (18)
H8A	−0.0704	0.1493	−0.4676	0.111*
H8B	−0.0736	0.2252	−0.3850	0.111*
H8C	−0.2261	0.1588	−0.4092	0.111*
C9	0.0213 (6)	0.1003 (3)	−0.0182 (4)	0.0424 (9)
H9A	0.0639	0.0834	0.0624	0.051*
H9B	0.0916	0.1481	−0.0291	0.051*
C10	−0.1610 (8)	0.1284 (4)	−0.0376 (7)	0.077 (2)
H10A	−0.2313	0.0808	−0.0260	0.093*
H10B	−0.2039	0.1451	−0.1183	0.093*
C11	−0.1954 (6)	0.1992 (3)	0.0362 (4)	0.0442 (10)
C20	0.0295 (6)	−0.1083 (3)	−0.3339 (4)	0.0376 (9)
H20	−0.0939	−0.0926	−0.3422	0.045*
C21	0.0324 (8)	−0.2007 (3)	−0.3684 (5)	0.0565 (12)
H21A	−0.0407	−0.2083	−0.4461	0.085*
H21B	−0.0118	−0.2346	−0.3159	0.085*
H21C	0.1514	−0.2171	−0.3647	0.085*
C22	0.0988 (5)	−0.0540 (3)	−0.4169 (4)	0.0402 (8)
C23	0.2743 (6)	−0.0335 (4)	−0.3950 (4)	0.0501 (10)
H23	0.3518	−0.0501	−0.3252	0.060*
C24	0.3401 (6)	0.0120 (5)	−0.4754 (4)	0.0647 (13)
H24	0.4602	0.0236	−0.4596	0.078*
C25	0.2281 (8)	0.0386 (4)	−0.5759 (4)	0.0638 (14)
H25	0.2727	0.0698	−0.6274	0.077*
C26	0.0470 (7)	0.0206 (4)	−0.6045 (4)	0.0548 (14)
C27	−0.0689 (9)	0.0509 (5)	−0.7070 (5)	0.0734 (17)
H27	−0.0245	0.0839	−0.7569	0.088*
C28	−0.2466 (10)	0.0330 (5)	−0.7358 (5)	0.086 (2)
H28	−0.3218	0.0528	−0.8046	0.103*
C29	−0.3114 (9)	−0.0157 (6)	−0.6591 (5)	0.086 (2)
H29	−0.4312	−0.0285	−0.6781	0.103*
C30	−0.2042 (7)	−0.0450 (4)	−0.5570 (5)	0.0640 (14)
H30	−0.2527	−0.0768	−0.5080	0.077*
C31	−0.0212 (7)	−0.0278 (3)	−0.5246 (4)	0.0465 (10)
C32	−0.4245 (13)	−0.2529 (7)	−0.2627 (9)	0.112 (3)
H32A	−0.2997	−0.2601	−0.2251	0.135*
H32B	−0.4825	−0.3062	−0.2600	0.135*
C33	−0.4461 (13)	−0.2296 (9)	−0.3833 (10)	0.131 (4)
H33A	−0.3989	−0.2731	−0.4218	0.196*
H33B	−0.3843	−0.1782	−0.3867	0.196*
H33C	−0.5694	−0.2223	−0.4211	0.196*
O10	−0.4969 (5)	−0.1910 (3)	−0.1986 (4)	0.0702 (11)
H010	−0.4280	−0.1516	−0.1809	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0308 (2)	0.0288 (2)	0.0313 (2)	−0.0003 (2)	0.00761 (15)	−0.0001 (2)
O1	0.0352 (14)	0.0411 (16)	0.074 (2)	−0.0030 (13)	0.0152 (14)	0.0061 (15)
O2	0.0483 (19)	0.077 (2)	0.070 (2)	0.0017 (18)	−0.0112 (18)	0.005 (2)
O3	0.0396 (16)	0.059 (2)	0.088 (3)	−0.0111 (16)	0.0138 (17)	−0.005 (2)
O4	0.0392 (14)	0.0562 (18)	0.0429 (15)	0.0050 (13)	0.0001 (12)	0.0042 (14)
O5	0.060 (2)	0.0426 (19)	0.074 (2)	−0.0069 (15)	0.0240 (17)	−0.0239 (16)
N1	0.0416 (17)	0.0301 (15)	0.0456 (18)	−0.0008 (14)	0.0208 (15)	0.0001 (14)
N2	0.047 (2)	0.045 (2)	0.0361 (17)	0.0040 (16)	−0.0010 (15)	−0.0008 (15)
N3	0.0383 (17)	0.0372 (17)	0.055 (2)	−0.0088 (15)	0.0166 (15)	−0.0063 (16)
N4	0.0397 (16)	0.0350 (17)	0.0346 (15)	0.0046 (14)	0.0101 (13)	0.0011 (13)
N5	0.051 (2)	0.052 (2)	0.085 (3)	0.0005 (19)	0.024 (2)	−0.025 (2)
N6	0.0384 (17)	0.0332 (16)	0.0380 (17)	0.0055 (13)	0.0151 (14)	0.0019 (13)
C1	0.063 (3)	0.036 (2)	0.046 (2)	0.002 (2)	0.023 (2)	0.0059 (17)
C2	0.070 (3)	0.040 (2)	0.037 (2)	0.009 (2)	0.012 (2)	0.0016 (18)
C3	0.064 (3)	0.040 (2)	0.058 (3)	−0.010 (2)	0.034 (2)	−0.004 (2)
C4	0.071 (3)	0.038 (2)	0.040 (2)	0.007 (2)	0.023 (2)	0.0102 (18)
C5	0.093 (5)	0.062 (3)	0.071 (4)	−0.007 (3)	0.042 (4)	0.017 (3)
C6	0.102 (5)	0.078 (4)	0.049 (3)	0.014 (4)	0.001 (3)	0.019 (3)
C7	0.096 (5)	0.060 (3)	0.104 (5)	−0.025 (3)	0.057 (4)	0.007 (3)
C8	0.105 (5)	0.066 (4)	0.050 (3)	0.015 (3)	0.020 (3)	0.027 (3)
C9	0.046 (2)	0.037 (2)	0.043 (2)	−0.0002 (18)	0.0101 (18)	−0.0130 (17)
C10	0.049 (3)	0.075 (4)	0.102 (5)	0.003 (3)	0.010 (3)	−0.057 (4)
C11	0.049 (2)	0.037 (2)	0.047 (2)	0.0059 (19)	0.0128 (19)	−0.0071 (18)
C20	0.0385 (19)	0.037 (2)	0.038 (2)	−0.0019 (16)	0.0108 (16)	−0.0051 (16)
C21	0.071 (3)	0.042 (2)	0.060 (3)	−0.003 (2)	0.023 (2)	−0.015 (2)
C22	0.0394 (19)	0.047 (2)	0.0369 (19)	−0.0031 (17)	0.0147 (16)	−0.0037 (17)
C23	0.039 (2)	0.068 (3)	0.045 (2)	−0.001 (2)	0.0136 (18)	0.000 (2)
C24	0.049 (2)	0.092 (4)	0.059 (3)	−0.016 (4)	0.0240 (19)	0.000 (4)
C25	0.069 (3)	0.082 (4)	0.047 (2)	−0.013 (3)	0.027 (2)	0.008 (2)
C26	0.068 (3)	0.063 (4)	0.036 (2)	−0.003 (2)	0.0172 (18)	0.000 (2)
C27	0.080 (4)	0.095 (5)	0.044 (3)	−0.005 (4)	0.016 (3)	0.007 (3)
C28	0.081 (4)	0.120 (7)	0.044 (3)	0.004 (4)	−0.004 (3)	0.013 (3)
C29	0.056 (3)	0.133 (8)	0.057 (3)	0.003 (4)	−0.006 (3)	−0.001 (4)
C30	0.051 (3)	0.091 (4)	0.047 (2)	−0.009 (3)	0.007 (2)	0.001 (3)
C31	0.050 (2)	0.055 (2)	0.037 (2)	0.000 (2)	0.0157 (18)	−0.0031 (18)
C32	0.101 (6)	0.120 (8)	0.124 (7)	−0.002 (6)	0.044 (6)	0.007 (6)
C33	0.091 (6)	0.164 (10)	0.139 (8)	0.001 (7)	0.033 (6)	−0.011 (9)
O10	0.055 (2)	0.071 (3)	0.087 (3)	−0.0196 (19)	0.022 (2)	0.008 (2)

Geometric parameters (Å, º)

Co1—N4	1.883 (3)	C8—H8C	0.9600
Co1—N2	1.887 (4)	C9—C10	1.459 (7)
Co1—N3	1.889 (3)	C9—H9A	0.9700
Co1—N1	1.890 (3)	C9—H9B	0.9700
Co1—C9	2.013 (4)	C10—C11	1.502 (6)
Co1—N6	2.092 (3)	C10—H10A	0.9700
O1—N1	1.338 (5)	C10—H10B	0.9700
O2—N2	1.357 (5)	C20—C22	1.523 (6)
O2—H02	1.008 (5)	C20—C21	1.534 (6)
O3—N3	1.328 (5)	C20—H20	0.9800
O4—N4	1.353 (5)	C21—H21A	0.9600
O4—H04	1.006 (3)	C21—H21B	0.9600
O5—C11	1.240 (6)	C21—H21C	0.9600
N1—C1	1.292 (6)	C22—C23	1.372 (6)
N2—C2	1.293 (7)	C22—C31	1.439 (7)
N3—C3	1.289 (7)	C23—C24	1.408 (7)
N4—C4	1.291 (6)	C23—H23	0.9300
N5—C11	1.313 (6)	C24—C25	1.354 (8)
N5—H05A	0.8600	C24—H24	0.9300
N5—H05B	0.8600	C25—C26	1.400 (8)
N6—C20	1.475 (6)	C25—H25	0.9300
N6—H06A	0.9000	C26—C27	1.403 (8)
N6—H06B	0.9000	C26—C31	1.439 (7)
C1—C2	1.468 (8)	C27—C28	1.375 (10)
C1—C5	1.493 (7)	C27—H27	0.9300
C2—C6	1.490 (7)	C28—C29	1.396 (11)
C3—C4	1.456 (8)	C28—H28	0.9300
C3—C7	1.506 (7)	C29—C30	1.367 (8)
C4—C8	1.509 (7)	C29—H29	0.9300
C5—H5A	0.9600	C30—C31	1.411 (7)
C5—H5B	0.9600	C30—H30	0.9300
C5—H5C	0.9600	C32—C33	1.454 (13)
C6—H6A	0.9600	C32—O10	1.455 (11)
C6—H6B	0.9600	C32—H32A	0.9700
C6—H6C	0.9600	C32—H32B	0.9700
C7—H7A	0.9600	C33—H33A	0.9600
C7—H7B	0.9600	C33—H33B	0.9600
C7—H7C	0.9600	C33—H33C	0.9600
C8—H8A	0.9600	O10—H010	0.8200
C8—H8B	0.9600
N4—Co1—N2	177.43 (16)	H8A—C8—H8C	109.5
N4—Co1—N3	81.53 (16)	H8B—C8—H8C	109.5
N2—Co1—N3	98.68 (17)	C10—C9—Co1	117.8 (3)
N4—Co1—N1	98.63 (16)	C10—C9—H9A	107.9
N2—Co1—N1	81.03 (17)	Co1—C9—H9A	107.9
N3—Co1—N1	177.11 (16)	C10—C9—H9B	107.9
N4—Co1—C9	88.89 (17)	Co1—C9—H9B	107.9
N2—Co1—C9	88.56 (18)	H9A—C9—H9B	107.2
N3—Co1—C9	87.83 (17)	C9—C10—C11	117.4 (5)
N1—Co1—C9	89.28 (17)	C9—C10—H10A	107.9
N4—Co1—N6	94.39 (14)	C11—C10—H10A	107.9
N2—Co1—N6	88.16 (15)	C9—C10—H10B	107.9
N3—Co1—N6	92.95 (15)	C11—C10—H10B	107.9
N1—Co1—N6	89.92 (14)	H10A—C10—H10B	107.2
C9—Co1—N6	176.71 (17)	O5—C11—N5	123.0 (4)
N2—O2—H02	96.5 (3)	O5—C11—C10	121.9 (4)
N4—O4—H04	96.5 (3)	N5—C11—C10	115.1 (4)
C1—N1—O1	121.5 (4)	N6—C20—C22	112.9 (3)
C1—N1—Co1	116.8 (3)	N6—C20—C21	110.9 (4)
O1—N1—Co1	121.8 (3)	C22—C20—C21	109.8 (4)
C2—N2—O2	119.3 (4)	N6—C20—H20	107.7
C2—N2—Co1	117.4 (3)	C22—C20—H20	107.7
O2—N2—Co1	123.3 (3)	C21—C20—H20	107.7
C3—N3—O3	122.0 (4)	C20—C21—H21A	109.5
C3—N3—Co1	116.3 (3)	C20—C21—H21B	109.5
O3—N3—Co1	121.8 (3)	H21A—C21—H21B	109.5
C4—N4—O4	120.0 (4)	C20—C21—H21C	109.5
C4—N4—Co1	116.2 (3)	H21A—C21—H21C	109.5
O4—N4—Co1	123.8 (3)	H21B—C21—H21C	109.5
C11—N5—H05A	120.0	C23—C22—C31	119.1 (4)
C11—N5—H05B	120.0	C23—C22—C20	121.8 (4)
H05A—N5—H05B	120.0	C31—C22—C20	119.0 (4)
C20—N6—Co1	120.6 (3)	C22—C23—C24	121.7 (4)
C20—N6—H06A	107.2	C22—C23—H23	119.1
Co1—N6—H06A	107.2	C24—C23—H23	119.1
C20—N6—H06B	107.2	C25—C24—C23	119.8 (4)
Co1—N6—H06B	107.2	C25—C24—H24	120.1
H06A—N6—H06B	106.8	C23—C24—H24	120.1
N1—C1—C2	112.8 (4)	C24—C25—C26	121.9 (5)
N1—C1—C5	123.1 (5)	C24—C25—H25	119.0
C2—C1—C5	124.1 (5)	C26—C25—H25	119.0
N2—C2—C1	112.0 (4)	C25—C26—C27	121.5 (5)
N2—C2—C6	123.7 (5)	C25—C26—C31	118.8 (4)
C1—C2—C6	124.3 (5)	C27—C26—C31	119.7 (5)
N3—C3—C4	112.8 (4)	C28—C27—C26	121.7 (6)
N3—C3—C7	122.5 (5)	C28—C27—H27	119.1
C4—C3—C7	124.6 (5)	C26—C27—H27	119.1
N4—C4—C3	113.1 (4)	C27—C28—C29	118.3 (6)
N4—C4—C8	121.7 (5)	C27—C28—H28	120.8
C3—C4—C8	125.2 (5)	C29—C28—H28	120.8
C1—C5—H5A	109.5	C30—C29—C28	122.1 (6)
C1—C5—H5B	109.5	C30—C29—H29	119.0
H5A—C5—H5B	109.5	C28—C29—H29	119.0
C1—C5—H5C	109.5	C29—C30—C31	121.2 (6)
H5A—C5—H5C	109.5	C29—C30—H30	119.4
H5B—C5—H5C	109.5	C31—C30—H30	119.4
C2—C6—H6A	109.5	C30—C31—C26	117.0 (5)
C2—C6—H6B	109.5	C30—C31—C22	124.4 (4)
H6A—C6—H6B	109.5	C26—C31—C22	118.6 (4)
C2—C6—H6C	109.5	C33—C32—O10	113.0 (9)
H6A—C6—H6C	109.5	C33—C32—H32A	109.0
H6B—C6—H6C	109.5	O10—C32—H32A	109.0
C3—C7—H7A	109.5	C33—C32—H32B	109.0
C3—C7—H7B	109.5	O10—C32—H32B	109.0
H7A—C7—H7B	109.5	H32A—C32—H32B	107.8
C3—C7—H7C	109.5	C32—C33—H33A	109.5
H7A—C7—H7C	109.5	C32—C33—H33B	109.5
H7B—C7—H7C	109.5	H33A—C33—H33B	109.5
C4—C8—H8A	109.5	C32—C33—H33C	109.5
C4—C8—H8B	109.5	H33A—C33—H33C	109.5
H8A—C8—H8B	109.5	H33B—C33—H33C	109.5
C4—C8—H8C	109.5	C32—O10—H010	109.5
N4—Co1—N1—C1	−175.3 (3)	N1—C1—C2—N2	1.7 (6)
N2—Co1—N1—C1	2.1 (3)	C5—C1—C2—N2	−179.1 (5)
N3—Co1—N1—C1	−82 (3)	N1—C1—C2—C6	−177.6 (5)
C9—Co1—N1—C1	−86.5 (3)	C5—C1—C2—C6	1.6 (8)
N6—Co1—N1—C1	90.3 (3)	O3—N3—C3—C4	179.1 (4)
N4—Co1—N1—O1	4.5 (3)	Co1—N3—C3—C4	−1.6 (5)
N2—Co1—N1—O1	−178.0 (3)	O3—N3—C3—C7	0.8 (7)
N3—Co1—N1—O1	98 (3)	Co1—N3—C3—C7	−179.8 (4)
C9—Co1—N1—O1	93.3 (3)	O4—N4—C4—C3	−179.6 (4)
N6—Co1—N1—O1	−89.9 (3)	Co1—N4—C4—C3	2.2 (5)
N4—Co1—N2—C2	82 (4)	O4—N4—C4—C8	1.1 (7)
N3—Co1—N2—C2	176.0 (3)	Co1—N4—C4—C8	−177.1 (4)
N1—Co1—N2—C2	−1.1 (3)	N3—C3—C4—N4	−0.4 (6)
C9—Co1—N2—C2	88.4 (4)	C7—C3—C4—N4	177.9 (5)
N6—Co1—N2—C2	−91.3 (4)	N3—C3—C4—C8	178.9 (5)
N4—Co1—N2—O2	−99 (4)	C7—C3—C4—C8	−2.9 (8)
N3—Co1—N2—O2	−4.7 (4)	N4—Co1—C9—C10	46.2 (5)
N1—Co1—N2—O2	178.2 (4)	N2—Co1—C9—C10	−133.5 (5)
C9—Co1—N2—O2	−92.3 (4)	N3—Co1—C9—C10	127.8 (5)
N6—Co1—N2—O2	88.0 (4)	N1—Co1—C9—C10	−52.5 (5)
N4—Co1—N3—C3	2.2 (3)	N6—Co1—C9—C10	−128 (3)
N2—Co1—N3—C3	−175.2 (3)	Co1—C9—C10—C11	−179.6 (4)
N1—Co1—N3—C3	−91 (3)	C9—C10—C11—O5	16.8 (9)
C9—Co1—N3—C3	−87.0 (4)	C9—C10—C11—N5	−163.4 (6)
N6—Co1—N3—C3	96.2 (3)	Co1—N6—C20—C22	81.1 (4)
N4—Co1—N3—O3	−178.5 (4)	Co1—N6—C20—C21	−155.2 (3)
N2—Co1—N3—O3	4.1 (4)	N6—C20—C22—C23	33.1 (6)
N1—Co1—N3—O3	88 (3)	C21—C20—C22—C23	−91.2 (5)
C9—Co1—N3—O3	92.3 (4)	N6—C20—C22—C31	−150.8 (4)
N6—Co1—N3—O3	−84.5 (3)	C21—C20—C22—C31	84.9 (5)
N2—Co1—N4—C4	92 (4)	C31—C22—C23—C24	−0.4 (8)
N3—Co1—N4—C4	−2.4 (3)	C20—C22—C23—C24	175.7 (5)
N1—Co1—N4—C4	174.7 (3)	C22—C23—C24—C25	1.9 (10)
C9—Co1—N4—C4	85.6 (3)	C23—C24—C25—C26	−1.6 (10)
N6—Co1—N4—C4	−94.7 (3)	C24—C25—C26—C27	177.9 (6)
N2—Co1—N4—O4	−86 (4)	C24—C25—C26—C31	−0.2 (9)
N3—Co1—N4—O4	179.4 (3)	C25—C26—C27—C28	179.6 (7)
N1—Co1—N4—O4	−3.5 (3)	C31—C26—C27—C28	−2.3 (10)
C9—Co1—N4—O4	−92.6 (3)	C26—C27—C28—C29	0.9 (12)
N6—Co1—N4—O4	87.1 (3)	C27—C28—C29—C30	0.6 (12)
N4—Co1—N6—C20	−10.8 (3)	C28—C29—C30—C31	−0.5 (12)
N2—Co1—N6—C20	168.9 (3)	C29—C30—C31—C26	−0.9 (9)
N3—Co1—N6—C20	−92.5 (3)	C29—C30—C31—C22	177.7 (6)
N1—Co1—N6—C20	87.8 (3)	C25—C26—C31—C30	−179.6 (5)
C9—Co1—N6—C20	164 (3)	C27—C26—C31—C30	2.3 (8)
O1—N1—C1—C2	177.5 (4)	C25—C26—C31—C22	1.7 (8)
Co1—N1—C1—C2	−2.7 (5)	C27—C26—C31—C22	−176.4 (5)
O1—N1—C1—C5	−1.7 (7)	C23—C22—C31—C30	−180.0 (5)
Co1—N1—C1—C5	178.1 (4)	C20—C22—C31—C30	3.9 (7)
O2—N2—C2—C1	−179.3 (4)	C23—C22—C31—C26	−1.4 (7)
Co1—N2—C2—C1	0.0 (5)	C20—C22—C31—C26	−177.5 (4)
O2—N2—C2—C6	0.0 (7)	C10—C11—N5—H05A	−179.8
Co1—N2—C2—C6	179.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H02···O3	1.008 (5)	1.482 (4)	2.491 (6)	179.7 (3)
O4—H04···O1	1.006 (3)	1.489 (3)	2.495 (5)	179.9 (3)
N6—H06A···O10^i	0.90	2.56	3.288 (6)	139
N6—H06B···O5^ii	0.90	2.09	2.993 (5)	177
N5—H05A···O10^iii	0.86	2.12	2.946 (5)	160
N5—H05B···O3^iv	0.86	2.14	2.980 (6)	167
O10—H010···O1	0.82	1.88	2.703 (5)	179

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

(II) Bis(dimethylglyoximato) [2-(methylcarbamoyl)ethyl][methyl (S)-phenylalaninate]cobalt(III)

Crystal data

[Co(C4H7N2O2)2(C4H8NO)(C10H13NO2)]	F(000) = 584
Mr = 554.49	Dx = 1.361 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 11.097 (4) Å	Cell parameters from 25 reflections
b = 10.914 (3) Å	θ = 12.5–15.0°
c = 11.178 (4) Å	µ = 0.68 mm^−1
β = 91.50 (3)°	T = 298 K
V = 1353.3 (7) Å^3	Prismatic, red
Z = 2	0.50 × 0.50 × 0.50 mm

Data collection

RIGAKU AFC5 diffractometer	2981 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.000
Graphite monochromator	θmax = 27.6°, θmin = 1.8°
ω/2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = 0→14
Tmin = 0.726, Tmax = 0.726	l = −14→14
3291 measured reflections	3 standard reflections every 100 reflections
3291 independent reflections	intensity decay: none

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.136	Calculated w = 1/[σ^2(Fo^2) + (0.1018P)^2 + 0.0925P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
3291 reflections	Δρmax = 1.40 e Å^−3
382 parameters	Δρmin = −0.29 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: −0.01 (2)

Special details

Experimental. (2-Carbamoylethyl)bis(dimethylglyoximato) [(R)-1-(1-naphthyl)ethylamine]cobalt(III) and bis(dimethylglyoximato) [2-(methylcarbamoyl)ethyl][methyl (S)-phenylalaninate]cobalt(III)

The preparation of the series of N-substituted cobaloxime complexes was basically carried out according to the literature methods with minor change·(Ohgo et al., 1996) The crystal was obtained by slow evaporation from ethanol/hexane solution.

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	0.20248 (4)	0.00909 (6)	−0.21730 (4)	0.03327 (16)
O1	0.0486 (4)	−0.1094 (4)	−0.3866 (4)	0.0502 (10)
O2	0.2132 (3)	0.2629 (3)	−0.1564 (3)	0.0516 (8)
H02	0.2670	0.2070	−0.1076	0.062*
O3	0.3461 (4)	0.1258 (4)	−0.0359 (4)	0.0545 (10)
O4	0.1994 (3)	−0.2445 (3)	−0.2845 (3)	0.0482 (7)
H04	0.1385	−0.1904	−0.3256	0.058*
O5	0.1633 (4)	−0.0294 (4)	0.1348 (4)	0.0613 (10)
O6	0.1077 (4)	0.1665 (4)	0.1633 (3)	0.0627 (10)
N1	0.0837 (3)	−0.0018 (5)	−0.3393 (3)	0.0387 (8)
N2	0.1621 (4)	0.1759 (4)	−0.2278 (3)	0.0412 (8)
N3	0.3210 (3)	0.0193 (5)	−0.0938 (3)	0.0403 (8)
N4	0.2482 (3)	−0.1577 (4)	−0.2113 (3)	0.0372 (7)
N6	0.0696 (3)	−0.0277 (4)	−0.0923 (3)	0.0391 (8)
H06A	0.0036	−0.0530	−0.1337	0.047*
H06B	0.0957	−0.0918	−0.0481	0.047*
C1	0.0311 (5)	0.0997 (6)	−0.3704 (5)	0.0431 (11)
C2	0.0792 (5)	0.2062 (5)	−0.3059 (4)	0.0443 (10)
C3	0.3744 (5)	−0.0804 (6)	−0.0638 (5)	0.0439 (12)
C4	0.3349 (4)	−0.1858 (5)	−0.1374 (4)	0.0416 (9)
C5	−0.0686 (5)	0.1072 (6)	−0.4624 (5)	0.0585 (14)
H5A	−0.0364	0.1311	−0.5377	0.088*
H5B	−0.1268	0.1666	−0.4380	0.088*
H5C	−0.1067	0.0285	−0.4705	0.088*
C6	0.0374 (6)	0.3348 (6)	−0.3259 (5)	0.0629 (14)
H6A	−0.0409	0.3451	−0.2929	0.094*
H6B	0.0332	0.3515	−0.4102	0.094*
H6C	0.0932	0.3904	−0.2875	0.094*
C7	0.4629 (5)	−0.0897 (6)	0.0398 (5)	0.0619 (14)
H7A	0.5421	−0.0695	0.0135	0.093*
H7B	0.4628	−0.1718	0.0707	0.093*
H7C	0.4403	−0.0337	0.1016	0.093*
C8	0.3915 (5)	−0.3097 (5)	−0.1295 (5)	0.0540 (12)
H8A	0.3946	−0.3362	−0.0476	0.081*
H8B	0.4717	−0.3060	−0.1593	0.081*
H8C	0.3444	−0.3667	−0.1766	0.081*
C20	0.0302 (4)	0.0673 (4)	−0.0082 (4)	0.0420 (9)
H20	0.0390	0.1480	−0.0454	0.050*
C28	0.1098 (5)	0.0614 (5)	0.1032 (4)	0.0480 (10)
C29	0.1772 (9)	0.1647 (10)	0.2758 (6)	0.091 (2)
H29A	0.1597	0.2371	0.3209	0.137*
H29B	0.2617	0.1624	0.2595	0.137*
H29C	0.1560	0.0935	0.3210	0.137*
C21	−0.1016 (4)	0.0502 (5)	0.0281 (4)	0.0485 (11)
H21A	−0.1107	−0.0297	0.0647	0.058*
H21B	−0.1217	0.1118	0.0868	0.058*
C22	−0.1866 (4)	0.0606 (5)	−0.0776 (4)	0.0478 (10)
C23	−0.2466 (5)	−0.0387 (7)	−0.1240 (7)	0.0663 (15)
H23	−0.2368	−0.1149	−0.0880	0.080*
C24	−0.3235 (6)	−0.0265 (9)	−0.2261 (8)	0.088 (3)
H24	−0.3627	−0.0949	−0.2581	0.106*
C25	−0.3399 (6)	0.0843 (10)	−0.2771 (6)	0.079 (2)
H25	−0.3913	0.0924	−0.3437	0.094*
C26	−0.2819 (6)	0.1841 (9)	−0.2319 (6)	0.078 (2)
H26	−0.2936	0.2602	−0.2678	0.093*
C27	−0.2060 (6)	0.1734 (6)	−0.1333 (6)	0.0606 (13)
H27	−0.1669	0.2426	−0.1033	0.073*
C9A	0.3340 (4)	0.0384 (5)	−0.3343 (4)	0.0538 (14)	0.503 (15)
H9A	0.3753	0.1126	−0.3088	0.065*	0.503 (15)
H9B	0.3914	−0.0281	−0.3238	0.065*	0.503 (15)
C10A	0.3099 (9)	0.0502 (15)	−0.4634 (6)	0.059 (4)	0.503 (15)
H10A	0.2623	0.1233	−0.4787	0.071*	0.503 (15)
H10B	0.2635	−0.0198	−0.4915	0.071*	0.503 (15)
C11A	0.4256 (10)	0.0579 (13)	−0.5314 (12)	0.057 (4)	0.503 (15)
O5A	0.4583 (12)	0.1597 (13)	−0.5661 (11)	0.086 (4)	0.503 (15)
N5A	0.4827 (13)	−0.0480 (16)	−0.5412 (15)	0.087 (7)	0.503 (15)
H05A	0.4457	−0.1145	−0.5233	0.105*	0.503 (15)
C12A	0.6097 (17)	−0.055 (3)	−0.582 (2)	0.130 (11)	0.503 (15)
H12A	0.6094	−0.0665	−0.6675	0.196*	0.503 (15)
H12B	0.6496	−0.1236	−0.5441	0.196*	0.503 (15)
H12C	0.6515	0.0189	−0.5616	0.196*	0.503 (15)
C9B	0.3340 (4)	0.0384 (5)	−0.3343 (4)	0.0538 (14)	0.497 (15)
H9C	0.3248	0.1207	−0.3660	0.065*	0.497 (15)
H9D	0.4109	0.0351	−0.2910	0.065*	0.497 (15)
C10B	0.3390 (14)	−0.0527 (15)	−0.4419 (11)	0.077 (5)	0.497 (15)
H10C	0.3551	−0.1339	−0.4100	0.093*	0.497 (15)
H10D	0.2596	−0.0550	−0.4804	0.093*	0.497 (15)
C11B	0.4302 (11)	−0.0266 (17)	−0.5369 (17)	0.078 (6)	0.497 (15)
O5B	0.4367 (12)	0.0751 (18)	−0.5820 (13)	0.090 (5)	0.497 (15)
N5B	0.5229 (13)	−0.1062 (15)	−0.5371 (14)	0.072 (4)	0.497 (15)
H05B	0.5236	−0.1705	−0.4925	0.086*	0.497 (15)
C12B	0.6250 (15)	−0.078 (2)	−0.6183 (15)	0.092 (6)	0.497 (15)
H12D	0.6340	0.0093	−0.6251	0.138*	0.497 (15)
H12E	0.6079	−0.1122	−0.6961	0.138*	0.497 (15)
H12F	0.6982	−0.1128	−0.5858	0.138*	0.497 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0312 (2)	0.0337 (2)	0.0347 (2)	0.0010 (2)	−0.00446 (16)	0.0005 (2)
O1	0.051 (2)	0.046 (2)	0.053 (2)	−0.0019 (17)	−0.0170 (16)	−0.0105 (16)
O2	0.068 (2)	0.0349 (16)	0.0514 (18)	−0.0050 (16)	−0.0133 (16)	−0.0013 (14)
O3	0.063 (2)	0.043 (2)	0.056 (2)	−0.0110 (18)	−0.0210 (19)	−0.0068 (16)
O4	0.0513 (17)	0.0406 (17)	0.0522 (18)	0.0034 (15)	−0.0084 (14)	−0.0113 (15)
O5	0.066 (2)	0.058 (2)	0.059 (2)	0.0046 (19)	−0.0072 (18)	0.0141 (17)
O6	0.077 (2)	0.061 (2)	0.0500 (19)	−0.001 (2)	−0.0081 (17)	−0.0113 (18)
N1	0.0353 (15)	0.042 (2)	0.0380 (15)	0.0006 (19)	−0.0066 (12)	−0.0005 (18)
N2	0.045 (2)	0.0386 (19)	0.0394 (18)	−0.0011 (17)	−0.0027 (14)	0.0008 (16)
N3	0.0366 (15)	0.044 (2)	0.0401 (15)	−0.007 (2)	−0.0070 (12)	0.001 (2)
N4	0.0328 (17)	0.0387 (18)	0.0399 (17)	0.0031 (15)	−0.0005 (13)	−0.0031 (15)
N6	0.0353 (16)	0.0404 (19)	0.0416 (18)	−0.0019 (14)	0.0019 (14)	−0.0001 (14)
C1	0.043 (2)	0.050 (3)	0.036 (2)	0.008 (2)	−0.0018 (18)	−0.001 (2)
C2	0.055 (3)	0.040 (2)	0.037 (2)	0.010 (2)	−0.0002 (18)	0.0043 (18)
C3	0.036 (2)	0.049 (3)	0.047 (2)	−0.005 (2)	−0.0090 (19)	0.007 (2)
C4	0.0350 (19)	0.040 (2)	0.049 (2)	0.0034 (18)	−0.0015 (17)	0.0021 (19)
C5	0.058 (3)	0.067 (3)	0.050 (3)	0.016 (3)	−0.017 (2)	0.000 (3)
C6	0.078 (4)	0.052 (3)	0.058 (3)	0.019 (3)	−0.008 (3)	0.004 (3)
C7	0.050 (3)	0.065 (3)	0.070 (3)	−0.001 (3)	−0.025 (2)	0.011 (3)
C8	0.050 (3)	0.047 (3)	0.065 (3)	0.015 (2)	−0.004 (2)	0.007 (2)
C20	0.043 (2)	0.039 (2)	0.044 (2)	0.0030 (18)	0.0019 (18)	0.0049 (18)
C28	0.050 (2)	0.049 (2)	0.045 (2)	−0.004 (2)	0.0031 (19)	0.002 (2)
C29	0.118 (6)	0.097 (6)	0.057 (3)	−0.005 (5)	−0.027 (4)	−0.017 (4)
C21	0.040 (2)	0.058 (3)	0.048 (2)	0.005 (2)	0.0083 (18)	0.002 (2)
C22	0.035 (2)	0.056 (3)	0.053 (2)	0.010 (2)	0.0067 (18)	0.000 (2)
C23	0.047 (3)	0.068 (4)	0.084 (4)	−0.011 (3)	0.006 (3)	0.001 (3)
C24	0.049 (3)	0.111 (7)	0.103 (6)	−0.018 (4)	−0.011 (4)	−0.012 (5)
C25	0.047 (3)	0.116 (6)	0.073 (4)	0.007 (4)	−0.009 (3)	0.007 (4)
C26	0.065 (4)	0.094 (6)	0.074 (4)	0.023 (4)	−0.006 (3)	0.018 (4)
C27	0.067 (3)	0.055 (3)	0.060 (3)	0.007 (3)	0.000 (2)	0.000 (3)
C9A	0.046 (2)	0.060 (4)	0.056 (3)	0.003 (2)	0.011 (2)	0.011 (2)
C10A	0.047 (5)	0.099 (11)	0.031 (4)	0.003 (6)	0.000 (4)	−0.004 (5)
C11A	0.049 (6)	0.081 (12)	0.043 (6)	−0.019 (7)	0.021 (6)	0.015 (7)
O5A	0.097 (8)	0.083 (9)	0.080 (7)	−0.020 (7)	0.040 (6)	−0.004 (6)
N5A	0.084 (14)	0.123 (18)	0.054 (8)	−0.020 (13)	−0.031 (9)	0.026 (10)
C12A	0.100 (14)	0.17 (2)	0.13 (2)	−0.001 (14)	0.088 (15)	−0.037 (17)
C9B	0.046 (2)	0.060 (4)	0.056 (3)	0.003 (2)	0.011 (2)	0.011 (2)
C10B	0.083 (10)	0.094 (13)	0.056 (7)	−0.005 (9)	0.019 (7)	−0.025 (8)
C11B	0.075 (13)	0.072 (12)	0.084 (12)	−0.015 (9)	−0.038 (10)	0.026 (9)
O5B	0.066 (6)	0.120 (12)	0.084 (9)	0.011 (7)	0.030 (7)	0.055 (10)
N5B	0.068 (8)	0.081 (10)	0.066 (8)	0.012 (7)	0.006 (6)	0.009 (7)
C12B	0.083 (11)	0.132 (16)	0.062 (9)	0.019 (11)	0.053 (8)	−0.004 (11)

Geometric parameters (Å, º)

Co1—N1	1.875 (3)	C20—C21	1.540 (6)
Co1—N2	1.878 (4)	C20—H20	0.9800
Co1—N3	1.885 (3)	C29—H29A	0.9600
Co1—N4	1.890 (4)	C29—H29B	0.9600
Co1—C9A	2.011 (5)	C29—H29C	0.9600
Co1—N6	2.096 (4)	C21—C22	1.497 (7)
O1—N1	1.342 (7)	C21—H21A	0.9700
O2—N2	1.356 (5)	C21—H21B	0.9700
O2—H02	1.004 (4)	C22—C23	1.367 (8)
O3—N3	1.356 (6)	C22—C27	1.394 (8)
O3—H02	1.471 (4)	C23—C24	1.413 (10)
O4—N4	1.356 (5)	C23—H23	0.9300
O4—H04	1.000 (3)	C24—C25	1.348 (13)
O5—C28	1.203 (6)	C24—H24	0.9300
O6—C28	1.329 (7)	C25—C26	1.356 (13)
O6—C29	1.458 (7)	C25—H25	0.9300
N1—C1	1.295 (8)	C26—C27	1.374 (9)
N2—C2	1.295 (6)	C26—H26	0.9300
N3—C3	1.279 (8)	C27—H27	0.9300
N4—C4	1.289 (6)	C9A—C10A	1.466 (8)
N6—C20	1.474 (6)	C9A—H9A	0.9700
N6—H06A	0.9000	C9A—H9B	0.9700
N6—H06B	0.9000	C10A—C11A	1.511 (9)
C1—C2	1.462 (8)	C10A—H10A	0.9700
C1—C5	1.493 (7)	C10A—H10B	0.9700
C2—C6	1.493 (7)	C11A—O5A	1.234 (10)
C3—C4	1.474 (7)	C11A—N5A	1.324 (10)
C3—C7	1.502 (7)	N5A—C12A	1.496 (10)
C4—C8	1.492 (7)	N5A—H05A	0.8600
C5—H5A	0.9600	C12A—H12A	0.9600
C5—H5B	0.9600	C12A—H12B	0.9600
C5—H5C	0.9600	C12A—H12C	0.9600
C6—H6A	0.9600	C10B—C11B	1.514 (10)
C6—H6B	0.9600	C10B—H10C	0.9700
C6—H6C	0.9600	C10B—H10D	0.9700
C7—H7A	0.9600	C11B—O5B	1.222 (10)
C7—H7B	0.9600	C11B—N5B	1.347 (9)
C7—H7C	0.9600	N5B—C12B	1.503 (9)
C8—H8A	0.9600	N5B—H05B	0.8600
C8—H8B	0.9600	C12B—H12D	0.9600
C8—H8C	0.9600	C12B—H12E	0.9600
C20—C28	1.509 (7)	C12B—H12F	0.9600
N1—Co1—N2	81.6 (2)	N6—C20—C28	108.6 (4)
N1—Co1—N3	179.53 (18)	N6—C20—C21	112.5 (4)
N2—Co1—N3	98.6 (2)	C28—C20—C21	108.5 (4)
N1—Co1—N4	98.51 (19)	N6—C20—H20	109.1
N2—Co1—N4	177.64 (17)	C28—C20—H20	109.1
N3—Co1—N4	81.3 (2)	C21—C20—H20	109.1
N1—Co1—C9A	92.62 (18)	O5—C28—O6	125.3 (5)
N2—Co1—C9A	88.9 (2)	O5—C28—C20	123.4 (5)
N3—Co1—C9A	87.82 (18)	O6—C28—C20	111.3 (4)
N4—Co1—C9A	88.71 (19)	O6—C29—H29A	109.5
N1—Co1—N6	88.82 (15)	O6—C29—H29B	109.5
N2—Co1—N6	93.23 (16)	H29A—C29—H29B	109.5
N3—Co1—N6	90.74 (15)	O6—C29—H29C	109.5
N4—Co1—N6	89.12 (15)	H29A—C29—H29C	109.5
C9A—Co1—N6	177.55 (19)	H29B—C29—H29C	109.5
N2—O2—H02	97.3 (3)	C22—C21—C20	111.5 (4)
N3—O3—H02	98.3 (3)	C22—C21—H21A	109.3
N4—O4—H04	96.8 (3)	C20—C21—H21A	109.3
C28—O6—C29	114.1 (5)	C22—C21—H21B	109.3
C1—N1—O1	121.2 (3)	C20—C21—H21B	109.3
C1—N1—Co1	116.4 (4)	H21A—C21—H21B	108.0
O1—N1—Co1	122.2 (4)	C23—C22—C27	117.6 (5)
C2—N2—O2	119.8 (4)	C23—C22—C21	122.0 (5)
C2—N2—Co1	117.0 (3)	C27—C22—C21	120.4 (5)
O2—N2—Co1	123.2 (3)	C22—C23—C24	120.6 (7)
C3—N3—O3	121.1 (4)	C22—C23—H23	119.7
C3—N3—Co1	116.8 (4)	C24—C23—H23	119.7
O3—N3—Co1	122.1 (4)	C25—C24—C23	119.8 (7)
C4—N4—O4	120.0 (4)	C25—C24—H24	120.1
C4—N4—Co1	116.6 (3)	C23—C24—H24	120.1
O4—N4—Co1	123.3 (3)	C24—C25—C26	120.4 (6)
C20—N6—Co1	121.1 (3)	C24—C25—H25	119.8
C20—N6—H06A	107.1	C26—C25—H25	119.8
Co1—N6—H06A	107.1	C25—C26—C27	120.3 (8)
C20—N6—H06B	107.1	C25—C26—H26	119.8
Co1—N6—H06B	107.1	C27—C26—H26	119.8
H06A—N6—H06B	106.8	C26—C27—C22	121.2 (7)
N1—C1—C2	113.0 (5)	C26—C27—H27	119.4
N1—C1—C5	123.5 (5)	C22—C27—H27	119.4
C2—C1—C5	123.4 (5)	C10A—C9A—Co1	122.5 (5)
N2—C2—C1	111.9 (4)	C10A—C9A—H9A	106.7
N2—C2—C6	123.7 (5)	Co1—C9A—H9A	106.7
C1—C2—C6	124.4 (5)	C10A—C9A—H9B	106.7
N3—C3—C4	112.9 (5)	Co1—C9A—H9B	106.7
N3—C3—C7	123.3 (6)	H9A—C9A—H9B	106.6
C4—C3—C7	123.8 (5)	C9A—C10A—C11A	111.4 (8)
N4—C4—C3	112.2 (4)	C9A—C10A—H10A	109.3
N4—C4—C8	124.0 (4)	C11A—C10A—H10A	109.3
C3—C4—C8	123.8 (4)	C9A—C10A—H10B	109.3
C1—C5—H5A	109.5	C11A—C10A—H10B	109.3
C1—C5—H5B	109.5	H10A—C10A—H10B	108.0
H5A—C5—H5B	109.5	O5A—C11A—N5A	127.9 (11)
C1—C5—H5C	109.5	O5A—C11A—C10A	117.9 (12)
H5A—C5—H5C	109.5	N5A—C11A—C10A	114.1 (12)
H5B—C5—H5C	109.5	C11A—N5A—C12A	122.0 (12)
C2—C6—H6A	109.5	C11A—N5A—H05A	119.0
C2—C6—H6B	109.5	C12A—N5A—H05A	119.0
H6A—C6—H6B	109.5	C11B—C10B—H10C	108.0
C2—C6—H6C	109.5	C11B—C10B—H10D	108.0
H6A—C6—H6C	109.5	H10C—C10B—H10D	107.2
H6B—C6—H6C	109.5	O5B—C11B—N5B	122.1 (12)
C3—C7—H7A	109.5	O5B—C11B—C10B	120.6 (14)
C3—C7—H7B	109.5	N5B—C11B—C10B	113.8 (13)
H7A—C7—H7B	109.5	C11B—N5B—C12B	117.1 (10)
C3—C7—H7C	109.5	C11B—N5B—H05B	121.4
H7A—C7—H7C	109.5	C12B—N5B—H05B	121.4
H7B—C7—H7C	109.5	N5B—C12B—H12D	109.5
C4—C8—H8A	109.5	N5B—C12B—H12E	109.5
C4—C8—H8B	109.5	H12D—C12B—H12E	109.5
H8A—C8—H8B	109.5	N5B—C12B—H12F	109.5
C4—C8—H8C	109.5	H12D—C12B—H12F	109.5
H8A—C8—H8C	109.5	H12E—C12B—H12F	109.5
H8B—C8—H8C	109.5
N2—Co1—N1—C1	−1.4 (4)	Co1—N2—C2—C6	−179.6 (4)
N3—Co1—N1—C1	112 (36)	N1—C1—C2—N2	−2.2 (6)
N4—Co1—N1—C1	−179.0 (4)	C5—C1—C2—N2	177.6 (5)
C9A—Co1—N1—C1	−89.9 (4)	N1—C1—C2—C6	178.5 (5)
N6—Co1—N1—C1	92.0 (4)	C5—C1—C2—C6	−1.7 (9)
N2—Co1—N1—O1	−176.9 (4)	O3—N3—C3—C4	−180.0 (4)
N3—Co1—N1—O1	−64 (36)	Co1—N3—C3—C4	2.5 (6)
N4—Co1—N1—O1	5.4 (4)	O3—N3—C3—C7	3.1 (8)
C9A—Co1—N1—O1	94.5 (4)	Co1—N3—C3—C7	−174.5 (4)
N6—Co1—N1—O1	−83.5 (4)	O4—N4—C4—C3	−178.8 (4)
N1—Co1—N2—C2	0.0 (3)	Co1—N4—C4—C3	4.9 (5)
N3—Co1—N2—C2	−179.5 (3)	O4—N4—C4—C8	2.9 (7)
N4—Co1—N2—C2	93 (4)	Co1—N4—C4—C8	−173.4 (4)
C9A—Co1—N2—C2	92.8 (4)	N3—C3—C4—N4	−4.8 (6)
N6—Co1—N2—C2	−88.3 (4)	C7—C3—C4—N4	172.1 (5)
N1—Co1—N2—O2	178.4 (4)	N3—C3—C4—C8	173.5 (4)
N3—Co1—N2—O2	−1.1 (4)	C7—C3—C4—C8	−9.6 (8)
N4—Co1—N2—O2	−88 (4)	Co1—N6—C20—C28	−89.1 (4)
C9A—Co1—N2—O2	−88.8 (4)	Co1—N6—C20—C21	150.8 (3)
N6—Co1—N2—O2	90.1 (4)	C29—O6—C28—O5	−0.4 (9)
N1—Co1—N3—C3	69 (36)	C29—O6—C28—C20	176.6 (5)
N2—Co1—N3—C3	−177.6 (4)	N6—C20—C28—O5	−24.3 (6)
N4—Co1—N3—C3	0.0 (4)	C21—C20—C28—O5	98.3 (6)
C9A—Co1—N3—C3	−89.0 (4)	N6—C20—C28—O6	158.7 (4)
N6—Co1—N3—C3	89.0 (4)	C21—C20—C28—O6	−78.8 (5)
N1—Co1—N3—O3	−108 (36)	N6—C20—C21—C22	−62.3 (5)
N2—Co1—N3—O3	4.9 (4)	C28—C20—C21—C22	177.5 (4)
N4—Co1—N3—O3	−177.5 (4)	C20—C21—C22—C23	109.2 (6)
C9A—Co1—N3—O3	93.5 (4)	C20—C21—C22—C27	−70.1 (6)
N6—Co1—N3—O3	−88.5 (4)	C27—C22—C23—C24	1.2 (9)
N1—Co1—N4—C4	177.5 (3)	C21—C22—C23—C24	−178.1 (5)
N2—Co1—N4—C4	85 (4)	C22—C23—C24—C25	−1.4 (11)
N3—Co1—N4—C4	−3.0 (3)	C23—C24—C25—C26	0.8 (12)
C9A—Co1—N4—C4	85.0 (3)	C24—C25—C26—C27	−0.2 (12)
N6—Co1—N4—C4	−93.9 (3)	C25—C26—C27—C22	0.1 (10)
N1—Co1—N4—O4	1.4 (3)	C23—C22—C27—C26	−0.6 (9)
N2—Co1—N4—O4	−91 (4)	C21—C22—C27—C26	178.7 (5)
N3—Co1—N4—O4	−179.1 (3)	N1—Co1—C9A—C10A	3.5 (9)
C9A—Co1—N4—O4	−91.1 (3)	N2—Co1—C9A—C10A	−78.1 (9)
N6—Co1—N4—O4	90.0 (3)	N3—Co1—C9A—C10A	−176.7 (9)
N1—Co1—N6—C20	−110.8 (3)	N4—Co1—C9A—C10A	101.9 (9)
N2—Co1—N6—C20	−29.3 (3)	N6—Co1—C9A—C10A	129 (4)
N3—Co1—N6—C20	69.3 (4)	Co1—C9A—C10A—C11A	−173.8 (8)
N4—Co1—N6—C20	150.6 (3)	C9A—C10A—C11A—O5A	−101.9 (16)
C9A—Co1—N6—C20	123 (4)	C9A—C10A—C11A—N5A	75.0 (17)
O1—N1—C1—C2	177.9 (5)	O5A—C11A—N5A—C12A	9 (3)
Co1—N1—C1—C2	2.3 (6)	O5B—C11B—N5B—C12B	−14 (3)
O1—N1—C1—C5	−1.9 (7)	Co1—C9B—C10B—C11B	174.9 (10)
Co1—N1—C1—C5	−177.5 (4)	C9B—C10B—C11B—N5B	109 (2)
O2—N2—C2—C1	−177.3 (4)	C10B—C11B—N5B—C12B	−172.7 (15)
Co1—N2—C2—C1	1.1 (5)	C10A—C11A—N5A—C12A	−167.1 (17)
O2—N2—C2—C6	2.0 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H02···O3	1.004 (4)	1.471 (4)	2.474 (6)	179.6 (3)
O4—H04···O1	1.000 (3)	1.486 (4)	2.486 (5)	179.7 (3)