An X-ray investigation of stereo­selectivity in the inter­actions of [Co(en)3]3+ with [Co(ox)3]3− (en is ethane-1,2-di­amine and ox is oxalate)

Gallagher, M.K.; Baker, J.; Black, R.; Oliver, A.G.; Lappin, A.G.

doi:10.1107/S2053229622002194

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An X-ray investigation of stereoselectivity in the interactions of [Co(en)₃]³⁺ with [Co(ox)₃]³⁻ (en is ethane-1,2-diamine and ox is oxalate)

M. K. Gallagher, J. Baker, R. Black, A. G. Oliver and A. G. Lappin

The X-ray structure of racemic tris(ethane-1,2-diamine-κ²N,N′)cobalt(III) tris(oxalato-κ²O¹,O²)cobaltate(III) pentahydrate, [Co(C₂H₈N₂)₃][Co(C₂O₄)₃]·5H₂O or [Co(en)₃][Co(ox)₃]·5H₂O, has been determined. Hydrogen-bonding interactions along the C₃-axis of the [Co(en)₃]³⁺ cation with the [Co(ox)₃]³⁻ anion are heterochiral, while those perpendicular to this axis are homochiral. Implications for the interpretation of chiral discriminations and induction in electron-transfer reactions in solution are discussed.

Keywords: hydrogen bonding; chiral interactions; crystal structure; cobalt; ethanediamine.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229622002194/ep3021sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229622002194/ep3021Isup2.hkl Contains datablock I

CCDC reference: 2076925

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b) and PLATON (Spek, 2020).

Tris(ethane-1,2-diamine-κ²N,N')cobalt(III) tris(oxalato-κ²O¹,O²)cobaltate(III) pentahydrate top

Crystal data top

[Co(C₂H₈N₂)₃][Co(C₂O₄)₃]·5H₂O	Z = 2
M_r = 652.31	F(000) = 676
Triclinic, P1	D_x = 1.684 Mg m⁻³
a = 8.606 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.153 (8) Å	Cell parameters from 2978 reflections
c = 13.562 (8) Å	θ = 2.2–24.7°
α = 77.480 (12)°	µ = 1.38 mm⁻¹
β = 74.393 (12)°	T = 120 K
γ = 72.198 (12)°	Block, green
V = 1286.7 (14) Å³	0.08 × 0.06 × 0.03 mm

Data collection top

Bruker APEXII diffractometer	5289 independent reflections
Radiation source: fine-focus sealed tube	3250 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm^-1	R_int = 0.113
combination of ω and φ–scans	θ_max = 26.6°, θ_min = 1.6°
Absorption correction: numerical (SADABS; Krause et al., 2015)	h = −10→10
T_min = 0.839, T_max = 1.000	k = −15→15
17566 measured reflections	l = −17→16

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.236	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.098P)² + 7.2608P] where P = (F_o² + 2F_c²)/3
5289 reflections	(Δ/σ)_max < 0.001
335 parameters	Δρ_max = 2.20 e Å⁻³
0 restraints	Δρ_min = −0.86 e Å⁻³

Special details top

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

Refinement. Data were treated with the SQUEEZE routine as implemented in PLATON (Spek, 2020). This was applied to account for two disordered water locations in the solvent channel. A detailed analysis of the SQUEEZE routine is provided at the end of this CIF. In summary two void spaces totaling 35 Å³ accounting for 16 electrons of density were corrected for.

Data were collected on a Bruker APEXII diffractometer using a combination of ω- and φ-scans of 0.5° (Bruker, 2014). The data were corrected for absorption and polarization effects and analysed for space group determination. The structure was solved by intrinsic phasing methods and expanded routinely (Sheldrick, 2015a). The model was refined by full-matrix least-squares analysis of F² against all reflections (Sheldrick, 2015b). All non-hydrogen atoms were refined with anisotropic atomic displacement parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Co1	0.04626 (13)	0.85797 (9)	0.26266 (7)	0.0142 (3)
N1	0.1474 (8)	0.9836 (5)	0.1894 (5)	0.0163 (14)
H1A	0.223006	0.988113	0.223054	0.020*
H1B	0.202769	0.967939	0.124548	0.020*
C1	0.0187 (10)	1.0974 (7)	0.1822 (6)	0.0202 (18)
H1C	−0.038896	1.104975	0.126011	0.024*
H1D	0.070418	1.163143	0.168470	0.024*
N2	−0.1520 (8)	0.9856 (6)	0.3089 (5)	0.0182 (15)
H2A	−0.233450	0.992466	0.275117	0.022*
H2B	−0.193170	0.968857	0.377975	0.022*
C2	−0.1037 (10)	1.0966 (6)	0.2868 (6)	0.0194 (17)
H2C	−0.050221	1.101647	0.341181	0.023*
H2D	−0.203406	1.163824	0.284478	0.023*
N3	0.1323 (8)	0.8467 (6)	0.3858 (5)	0.0182 (15)
H3A	0.115293	0.919527	0.400848	0.022*
H3B	0.076962	0.805695	0.441083	0.022*
C3	0.3143 (10)	0.7870 (7)	0.3656 (6)	0.0241 (19)
H3C	0.351172	0.755389	0.431658	0.029*
H3D	0.379520	0.842570	0.324828	0.029*
N4	0.2534 (8)	0.7400 (6)	0.2189 (5)	0.0182 (14)
H4A	0.229628	0.682216	0.197355	0.022*
H4B	0.321409	0.773047	0.164719	0.022*
C4	0.3406 (11)	0.6894 (7)	0.3060 (6)	0.025 (2)
H4C	0.461427	0.656403	0.279160	0.030*
H4D	0.293633	0.626346	0.351338	0.030*
N5	−0.0775 (8)	0.7412 (6)	0.3312 (5)	0.0215 (16)
H5A	−0.007091	0.668074	0.330332	0.026*
H5B	−0.124392	0.751736	0.398243	0.026*
C5	−0.2127 (10)	0.7553 (8)	0.2735 (6)	0.027 (2)
H5C	−0.258265	0.686139	0.293465	0.033*
H5D	−0.305276	0.825616	0.288970	0.033*
N6	−0.0292 (8)	0.8532 (6)	0.1399 (5)	0.0205 (15)
H6A	−0.092179	0.925438	0.119016	0.025*
H6B	0.061423	0.834135	0.087604	0.025*
C6	−0.1288 (11)	0.7677 (7)	0.1601 (6)	0.026 (2)
H6C	−0.055245	0.691230	0.141996	0.032*
H6D	−0.214104	0.794966	0.117432	0.032*
Co2	0.40708 (13)	0.20495 (9)	0.22434 (8)	0.0166 (3)
O1	0.5122 (7)	0.3254 (5)	0.1591 (4)	0.0244 (13)
O2	0.4514 (9)	0.5212 (6)	0.1312 (5)	0.0432 (19)
O3	0.2105 (7)	0.3265 (5)	0.2609 (4)	0.0239 (13)
O4	0.1291 (8)	0.5207 (5)	0.2452 (5)	0.0352 (16)
O5	0.3502 (7)	0.2066 (5)	0.0969 (4)	0.0223 (13)
O6	0.4847 (7)	0.1597 (5)	−0.0605 (4)	0.0280 (14)
O7	0.6047 (7)	0.0912 (5)	0.1770 (4)	0.0203 (13)
O8	0.7616 (7)	0.0379 (5)	0.0266 (4)	0.0196 (12)
O9	0.4707 (7)	0.1998 (5)	0.3494 (4)	0.0226 (13)
O10	0.3867 (7)	0.1436 (5)	0.5194 (4)	0.0277 (14)
O11	0.2948 (7)	0.0896 (5)	0.3015 (4)	0.0186 (12)
O12	0.1876 (7)	0.0315 (5)	0.4662 (4)	0.0221 (13)
C7	0.4142 (11)	0.4291 (7)	0.1666 (6)	0.0244 (19)
C8	0.2372 (11)	0.4292 (8)	0.2297 (6)	0.028 (2)
C9	0.4781 (11)	0.1558 (7)	0.0302 (6)	0.0232 (19)
C10	0.6279 (10)	0.0896 (6)	0.0794 (6)	0.0156 (16)
C11	0.3844 (9)	0.1458 (7)	0.4282 (6)	0.0182 (17)
C12	0.2797 (9)	0.0827 (7)	0.3991 (6)	0.0163 (16)
O1W	0.8017 (9)	0.3070 (6)	0.0032 (5)	0.0389 (17)
O2W	0.0117 (10)	0.6648 (7)	0.5452 (6)	0.060 (2)
O3W	0.7696 (18)	0.5582 (9)	0.0160 (9)	0.109 (4)
O4W	0.7888 (16)	0.4817 (10)	0.2236 (9)	0.104 (4)
O5W	0.5501 (16)	0.3926 (8)	0.3852 (8)	0.091 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0156 (6)	0.0149 (5)	0.0078 (5)	−0.0012 (4)	0.0034 (4)	−0.0046 (4)
N1	0.021 (3)	0.013 (3)	0.014 (3)	0.003 (3)	−0.004 (3)	−0.009 (3)
C1	0.022 (4)	0.018 (4)	0.016 (4)	−0.001 (3)	−0.005 (3)	0.001 (3)
N2	0.017 (3)	0.021 (4)	0.011 (3)	−0.002 (3)	−0.001 (3)	0.001 (3)
C2	0.021 (4)	0.011 (4)	0.020 (4)	0.002 (3)	0.001 (3)	−0.004 (3)
N3	0.018 (3)	0.015 (3)	0.015 (3)	−0.002 (3)	0.005 (3)	−0.002 (3)
C3	0.022 (4)	0.025 (5)	0.020 (4)	0.000 (4)	−0.001 (3)	−0.007 (3)
N4	0.022 (4)	0.015 (3)	0.015 (3)	−0.005 (3)	−0.001 (3)	−0.003 (3)
C4	0.025 (5)	0.025 (4)	0.017 (4)	0.003 (4)	0.002 (3)	−0.006 (3)
N5	0.020 (4)	0.021 (4)	0.016 (3)	−0.002 (3)	0.004 (3)	−0.002 (3)
C5	0.018 (4)	0.037 (5)	0.027 (5)	−0.005 (4)	0.001 (3)	−0.015 (4)
N6	0.016 (3)	0.021 (4)	0.020 (4)	−0.002 (3)	−0.002 (3)	−0.003 (3)
C6	0.034 (5)	0.020 (4)	0.025 (5)	−0.006 (4)	−0.006 (4)	−0.004 (4)
Co2	0.0194 (6)	0.0156 (6)	0.0100 (5)	−0.0017 (4)	0.0030 (4)	−0.0042 (4)
O1	0.023 (3)	0.021 (3)	0.023 (3)	−0.008 (2)	0.009 (2)	−0.007 (2)
O2	0.048 (4)	0.026 (4)	0.043 (4)	−0.012 (3)	0.016 (3)	−0.008 (3)
O3	0.024 (3)	0.020 (3)	0.019 (3)	−0.006 (2)	0.009 (2)	−0.003 (2)
O4	0.029 (4)	0.025 (3)	0.039 (4)	0.002 (3)	0.006 (3)	−0.008 (3)
O5	0.018 (3)	0.026 (3)	0.016 (3)	−0.002 (2)	0.001 (2)	0.000 (2)
O6	0.028 (3)	0.037 (4)	0.017 (3)	−0.006 (3)	−0.002 (2)	−0.005 (3)
O7	0.024 (3)	0.022 (3)	0.012 (3)	−0.003 (2)	−0.002 (2)	−0.005 (2)
O8	0.022 (3)	0.019 (3)	0.010 (3)	0.003 (2)	0.001 (2)	−0.004 (2)
O9	0.026 (3)	0.022 (3)	0.019 (3)	−0.006 (2)	0.002 (2)	−0.010 (2)
O10	0.029 (3)	0.040 (4)	0.018 (3)	−0.012 (3)	0.001 (2)	−0.015 (3)
O11	0.029 (3)	0.021 (3)	0.007 (2)	−0.009 (2)	−0.001 (2)	−0.004 (2)
O12	0.022 (3)	0.022 (3)	0.017 (3)	−0.004 (2)	−0.002 (2)	0.000 (2)
C7	0.031 (5)	0.017 (4)	0.021 (4)	−0.006 (4)	0.003 (4)	−0.004 (3)
C8	0.031 (5)	0.022 (5)	0.022 (4)	0.001 (4)	0.000 (4)	−0.006 (4)
C9	0.028 (5)	0.026 (5)	0.017 (4)	−0.013 (4)	0.001 (3)	−0.005 (3)
C10	0.020 (4)	0.013 (4)	0.011 (4)	−0.010 (3)	0.007 (3)	0.000 (3)
C11	0.015 (4)	0.026 (4)	0.013 (4)	−0.005 (3)	0.003 (3)	−0.010 (3)
C12	0.010 (4)	0.019 (4)	0.018 (4)	0.001 (3)	0.001 (3)	−0.010 (3)
O1W	0.047 (4)	0.030 (4)	0.032 (4)	−0.007 (3)	0.010 (3)	−0.015 (3)
O2W	0.066 (5)	0.049 (5)	0.033 (4)	−0.002 (4)	0.016 (4)	0.009 (4)
O3W	0.160 (12)	0.072 (7)	0.092 (8)	−0.013 (7)	−0.048 (8)	−0.009 (6)
O4W	0.119 (10)	0.103 (9)	0.103 (9)	−0.065 (8)	−0.002 (7)	−0.022 (7)
O5W	0.150 (11)	0.060 (6)	0.081 (7)	−0.039 (7)	−0.028 (7)	−0.025 (5)

Geometric parameters (Å, º) top

Co1—N1	1.940 (7)	N5—H5B	0.9100
Co1—N4	1.955 (6)	C5—C6	1.509 (12)
Co1—N5	1.957 (7)	C5—H5C	0.9900
Co1—N6	1.961 (7)	C5—H5D	0.9900
Co1—N3	1.965 (7)	N6—C6	1.478 (11)
Co1—N2	1.985 (6)	N6—H6A	0.9100
N1—C1	1.487 (9)	N6—H6B	0.9100
N1—H1A	0.9100	C6—H6C	0.9900
N1—H1B	0.9100	C6—H6D	0.9900
C1—C2	1.522 (11)	Co2—O1	1.887 (6)
C1—H1C	0.9900	Co2—O7	1.891 (5)
C1—H1D	0.9900	Co2—O9	1.900 (6)
N2—C2	1.477 (10)	Co2—O3	1.905 (6)
N2—H2A	0.9100	Co2—O11	1.909 (5)
N2—H2B	0.9100	Co2—O5	1.913 (6)
C2—H2C	0.9900	O1—C7	1.293 (10)
C2—H2D	0.9900	O2—C7	1.220 (10)
N3—C3	1.489 (10)	O3—C8	1.297 (11)
N3—H3A	0.9100	O4—C8	1.228 (10)
N3—H3B	0.9100	O5—C9	1.304 (10)
C3—C4	1.504 (12)	O6—C9	1.208 (10)
C3—H3C	0.9900	O7—C10	1.288 (9)
C3—H3D	0.9900	O8—C10	1.241 (9)
N4—C4	1.490 (10)	O9—C11	1.300 (9)
N4—H4A	0.9100	O10—C11	1.237 (9)
N4—H4B	0.9100	O11—C12	1.281 (9)
C4—H4C	0.9900	O12—C12	1.229 (9)
C4—H4D	0.9900	C7—C8	1.533 (12)
N5—C5	1.518 (11)	C9—C10	1.533 (12)
N5—H5A	0.9100	C11—C12	1.517 (11)

N1—Co1—N4	91.5 (3)	C5—N5—Co1	108.1 (5)
N1—Co1—N5	173.8 (3)	C5—N5—H5A	110.1
N4—Co1—N5	93.2 (3)	Co1—N5—H5A	110.1
N1—Co1—N6	91.1 (3)	C5—N5—H5B	110.1
N4—Co1—N6	90.0 (3)	Co1—N5—H5B	110.1
N5—Co1—N6	84.9 (3)	H5A—N5—H5B	108.4
N1—Co1—N3	92.1 (3)	C6—C5—N5	105.7 (7)
N4—Co1—N3	85.5 (3)	C6—C5—H5C	110.6
N5—Co1—N3	92.3 (3)	N5—C5—H5C	110.6
N6—Co1—N3	174.5 (3)	C6—C5—H5D	110.6
N1—Co1—N2	84.7 (3)	N5—C5—H5D	110.6
N4—Co1—N2	175.1 (3)	H5C—C5—H5D	108.7
N5—Co1—N2	90.8 (3)	C6—N6—Co1	112.1 (5)
N6—Co1—N2	93.2 (3)	C6—N6—H6A	109.2
N3—Co1—N2	91.5 (3)	Co1—N6—H6A	109.2
C1—N1—Co1	111.1 (5)	C6—N6—H6B	109.2
C1—N1—H1A	109.4	Co1—N6—H6B	109.2
Co1—N1—H1A	109.4	H6A—N6—H6B	107.9
C1—N1—H1B	109.4	N6—C6—C5	108.3 (7)
Co1—N1—H1B	109.4	N6—C6—H6C	110.0
H1A—N1—H1B	108.0	C5—C6—H6C	110.0
N1—C1—C2	105.5 (6)	N6—C6—H6D	110.0
N1—C1—H1C	110.6	C5—C6—H6D	110.0
C2—C1—H1C	110.6	H6C—C6—H6D	108.4
N1—C1—H1D	110.6	O1—Co2—O7	90.6 (2)
C2—C1—H1D	110.6	O1—Co2—O9	90.6 (3)
H1C—C1—H1D	108.8	O7—Co2—O9	92.4 (2)
C2—N2—Co1	109.5 (5)	O1—Co2—O3	86.1 (2)
C2—N2—H2A	109.8	O7—Co2—O3	175.3 (2)
Co1—N2—H2A	109.8	O9—Co2—O3	90.9 (2)
C2—N2—H2B	109.8	O1—Co2—O11	174.8 (2)
Co1—N2—H2B	109.8	O7—Co2—O11	92.7 (2)
H2A—N2—H2B	108.2	O9—Co2—O11	85.2 (2)
N2—C2—C1	106.9 (6)	O3—Co2—O11	90.8 (2)
N2—C2—H2C	110.3	O1—Co2—O5	89.3 (3)
C1—C2—H2C	110.3	O7—Co2—O5	85.6 (2)
N2—C2—H2D	110.3	O9—Co2—O5	178.1 (2)
C1—C2—H2D	110.3	O3—Co2—O5	91.0 (2)
H2C—C2—H2D	108.6	O11—Co2—O5	95.0 (2)
C3—N3—Co1	109.2 (5)	C7—O1—Co2	113.7 (5)
C3—N3—H3A	109.8	C8—O3—Co2	112.0 (5)
Co1—N3—H3A	109.8	C9—O5—Co2	112.3 (5)
C3—N3—H3B	109.8	C10—O7—Co2	111.2 (5)
Co1—N3—H3B	109.8	C11—O9—Co2	111.7 (5)
H3A—N3—H3B	108.3	C12—O11—Co2	111.8 (5)
N3—C3—C4	107.1 (7)	O2—C7—O1	126.5 (8)
N3—C3—H3C	110.3	O2—C7—C8	120.2 (8)
C4—C3—H3C	110.3	O1—C7—C8	113.3 (7)
N3—C3—H3D	110.3	O4—C8—O3	123.6 (8)
C4—C3—H3D	110.3	O4—C8—C7	121.6 (8)
H3C—C3—H3D	108.5	O3—C8—C7	114.8 (7)
C4—N4—Co1	110.3 (5)	O6—C9—O5	126.1 (8)
C4—N4—H4A	109.6	O6—C9—C10	121.8 (7)
Co1—N4—H4A	109.6	O5—C9—C10	112.0 (7)
C4—N4—H4B	109.6	O8—C10—O7	123.4 (7)
Co1—N4—H4B	109.6	O8—C10—C9	120.7 (7)
H4A—N4—H4B	108.1	O7—C10—C9	115.9 (6)
N4—C4—C3	107.1 (6)	O10—C11—O9	124.2 (8)
N4—C4—H4C	110.3	O10—C11—C12	121.8 (7)
C3—C4—H4C	110.3	O9—C11—C12	114.0 (6)
N4—C4—H4D	110.3	O12—C12—O11	124.6 (7)
C3—C4—H4D	110.3	O12—C12—C11	120.8 (7)
H4C—C4—H4D	108.5	O11—C12—C11	114.6 (7)

Co1—N1—C1—C2	40.0 (7)	O2—C7—C8—O4	0.6 (14)
Co1—N2—C2—C1	39.1 (7)	O1—C7—C8—O4	179.2 (8)
N1—C1—C2—N2	−50.7 (8)	O2—C7—C8—O3	178.1 (8)
Co1—N3—C3—C4	−39.8 (7)	O1—C7—C8—O3	−3.4 (11)
Co1—N4—C4—C3	−36.5 (8)	Co2—O5—C9—O6	−168.0 (7)
N3—C3—C4—N4	49.3 (8)	Co2—O5—C9—C10	10.8 (8)
Co1—N5—C5—C6	45.4 (7)	Co2—O7—C10—O8	167.1 (6)
Co1—N6—C6—C5	27.9 (8)	Co2—O7—C10—C9	−13.4 (8)
N5—C5—C6—N6	−46.9 (8)	O6—C9—C10—O8	0.1 (12)
O7—Co2—O1—C7	176.6 (6)	O5—C9—C10—O8	−178.7 (7)
O9—Co2—O1—C7	−90.9 (6)	O6—C9—C10—O7	−179.4 (8)
O3—Co2—O1—C7	0.0 (6)	O5—C9—C10—O7	1.7 (10)
O5—Co2—O1—C7	91.0 (6)	Co2—O9—C11—O10	−170.4 (6)
O1—Co2—O7—C10	−73.8 (5)	Co2—O9—C11—C12	10.4 (8)
O9—Co2—O7—C10	−164.4 (5)	Co2—O11—C12—O12	166.3 (6)
O11—Co2—O7—C10	110.2 (5)	Co2—O11—C12—C11	−12.6 (8)
O5—Co2—O7—C10	15.4 (5)	O10—C11—C12—O12	3.3 (11)
Co2—O1—C7—O2	−179.9 (8)	O9—C11—C12—O12	−177.5 (7)
Co2—O1—C7—C8	1.7 (9)	O10—C11—C12—O11	−177.7 (7)
Co2—O3—C8—O4	−179.4 (7)	O9—C11—C12—O11	1.5 (9)
Co2—O3—C8—C7	3.2 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O11ⁱ	0.91	2.10	2.910 (8)	147
N1—H1B···O8ⁱⁱ	0.91	2.00	2.869 (8)	159
N2—H2A···O7ⁱⁱⁱ	0.91	2.11	2.934 (8)	151
N2—H2B···O10^iv	0.91	2.43	3.129 (9)	134
N2—H2B···O12^iv	0.91	2.13	2.951 (8)	150
N3—H3A···O12ⁱ	0.91	2.09	2.906 (9)	149
N3—H3B···O2W	0.91	2.09	2.960 (10)	161
N4—H4A···O2	0.91	2.42	2.983 (9)	121
N4—H4A···O4	0.91	2.28	3.082 (10)	147
N4—H4B···O6ⁱⁱ	0.91	2.12	3.020 (9)	168
N5—H5A···O4	0.91	2.19	3.005 (9)	149
N5—H5B···O10^iv	0.91	2.34	3.033 (9)	133
N5—H5B···O2W	0.91	2.46	3.077 (11)	125
N6—H6A···O8ⁱⁱⁱ	0.91	2.02	2.857 (8)	152
N6—H6B···O8ⁱⁱ	0.91	2.50	3.151 (9)	128
N6—H6B···O1Wⁱⁱ	0.91	2.18	2.942 (9)	141

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

Interionic hydrogen-bonding graph-set notation for oxalate-containing complexes with the major symmetry axes of Δ-[Co(en)3]3+ (see Fig. 4) top

Metal–metal distance (Å)	Axis of interaction	Stereoselectivity of anion	Graph-set notation
[Rh(ox)₃]^3- (Kuroda, 1991)
4.905	C₃	Δ	R₁²(4)R₂¹(6)R₂²(8)R₁²(4)
			R₂¹(6)R₂²(8)R₁²(4)R₂¹(6)\ R₂²(8)
4.972	C₃	Δ	R₂²(8)R₂²(8)R₂²(8)
7.730	C₂	Δ	R₁²(5)R₂¹(6)R₂²(9)
[Cr(ox)₃]^3- (Hua et al., 2001)
4.948	C₃	Δ	R₁²(4)R₂¹(6)R₂²(8)R₁²(4)
			R₂¹(6)R₂²(8)R₁²(4)R₂¹(6)\ R₂²(8)
5.022	C₃	Δ	R₂²(8)R₂²(8)R₂²(8)
7.724	C₂	Δ	R₁²(5)R₂¹(6)R₂²(9)
[Cr(ox)₃]^3-^a (Hua et al., 2001)
4.983	C₃	Δ	R₂²(8)R₂²(8)R₂²(8)
5.061	C₃	Δ	R₁²(5)R₂¹(6)R₂²(9)
7.771	C₂	Δ	R₁²(5)R₂¹(6)R₂²(9)
[Rh(ox)₃]^3- (Kuroda, 1991)
5.121	C₃	Λ^b	R₂²(8)R₂²(8)R₂²(8)
7.564	C₃	Δ^c	R₁²(5)R₂¹(6)R₂²(9)
5.452	C₂	Δ/Λ	R₂²(8)
7.764	C₂	Δ/Λ	R₂¹(6)
7.681	C₂	Δ/Λ	R₂¹(6)
[Co(ox)₃]^3- (this work)
7.009 (4)	C₃	Δ	\ R₁²(5)R₂¹(6)R₂¹(6)R₂²(9)\ R₂²(9)R₂²(9)
7.044 (4)	C₃	Δ	R₂¹(6)R₂²(9)R₂²(9)
7.665 (5)	C₂	Λ	R₁²(5)R₂¹(6)R₂²(9)
5.821 (3)	C₂	Λ	R₂²(8)
5.892 (3)	C₂	Λ	R₂²(8)
[Co(gly)(ox)₂]^2- (Lappin et al., 1993)
5.686	C₃	Λ	R₁²(4)R₂¹(6)R₂¹(6)R₂²(8)^d
5.750	C₃	Λ	R₂¹(6)R₂²(8)R₂²(8)
6.664	C₂	Λ	R₂¹(6)
7.688	C₂	Λ	R₂¹(6)
[Co(en)(ox)₂]^- (Lappin et al., 1993)
6.139	C₃	Λ	R₂²(8)
6.145	C₃	Λ	R₂²(8)
7.527	C₂	Λ	R₂²(9)
7.564	C₂	Λ	R₂²(9)
7.229	C₃	Δ	R₁²(5)R₂¹(6)R₂¹(6)R₂²(9)
5.707	C₂	Δ	R₂²(8)^e
6.227	C₂	Δ	R₂²(8)
7.806	C₂	Δ	R₁²(5)

Notes: (a) The cation is [Cr(en)₃]³⁺; (b) the preference deduced from hydrogen bonding in the disorder model in the structure ΔΛ versus single hydrogen-bond for ΔΔ C₃. (c) ΔΔ preferred C₃ R₁²(5) ΔΛ. (d) bridging H₂O R₁²(6)R₁²(8)R₂²(10)R₂²(10)R₂²(12), (e) bridge to H₂O on C₃ R₂²(10)R₂²(12)R₂²(12)R₂²(14)R₂²(14). Standard uncertainties for previously published structures cannot be obtained.

Hydrogen-bond geometry (Å, °) for [Co(en)3][Co(ox)3].5(H2O) top

O1W···O1			2.785 (8)
O1W···O2ⁱⁱ			3.182 (10)
O1W···O3W			3.019 (13)
O2W···O3W^iv			2.806 (9)
O3W···O2			2.879 (16)
O3W···O5ⁱⁱ			2.955 (12)
O3W···O1W			3.019 (13)
O3W···O4W			2.780 (17)
O4W···O4^vi			3.202 (14)
O4W···O3W			2.780 (17)
O4W···O5W			2.848 (16)
O5W···O9			2.801 (11)
O5W···O4W			2.848 (16)

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

Crystal data and structure refinement parameters of 1 top

Empirical formula

Formula weight

Temperature (K)

Wavelength (Å)

Crystal system

Space group

a (Å)

b (Å) c (Å)

α (°)

β (°)

γ (°)

Volume (Å³)

Z, Z'

Density (calc.) (Mg m^-3)

Measured 2θ range

Stepsize (°)

Measured data points

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An X-ray investigation of stereo­selectivity in the inter­actions of [Co(en)3]3+ with [Co(ox)3]3− (en is ethane-1,2-di­amine and ox is oxalate)

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An X-ray investigation of stereoselectivity in the interactions of [Co(en)₃]³⁺ with [Co(ox)₃]³⁻ (en is ethane-1,2-diamine and ox is oxalate)