Reactivity trends of cobalt(III) com­plexes towards various amino acids based on the properties of the amino acid alkyl chains

The reactivity of the cobalt(III) com­plexes di­chlorido­[tris­(2-amino­eth­yl)am­ine]­cobalt(III) chloride, [CoCl₂(tren)]Cl, and di­chlorido­(tri­ethyl­ene­tetra­m­ine)cobalt(III) chloride, [CoCl₂(trien)]Cl, towards different amino acids (L-pro­line, L-asparagine, L-histidine and L-aspartic acid) was explored in detail. This study presents the crystal structures of three amino acidate cobalt(III) com­plexes, namely, (L-prolinato-κ²N,O)[tris­(2-amino­eth­yl)amine-κ⁴N,N′,N′′,N′′′]cobalt(III) diiodide monohydrate, [Co(C₅H₈NO₂)(C₆H₁₈N₄)]I₂·H₂O, I, (L-asparaginato-κ²N,O)[tris­(2-amino­eth­yl)amine-κ⁴N,N′,N′′,N′′′]cobalt(III) chlo­ride perchlorate, [Co(C₄H₇N₂O₃)(C₆H₁₈N₄)](Cl)(ClO₄), II, and (L-prolinato-κ²N,O)(tri­ethyl­ene­tetra­mine-κ⁴N,N′,N′′,N′′′)cobalt(III) chloride perchlorate, [Co(C₄H₇N₂O₃)(C₆H₁₈N₄)](Cl)(ClO₄), V. The syntheses of the com­plexes were followed by characterization using UV–Vis spectroscopy of the reaction mix­tures and the initial rates of reaction were obtained by calculating the slopes of absorbance versus time plots. The initial rates suggest a stronger reactivity and hence greater affinity of the cobalt(III) com­plexes towards basic amino acids. The biocom­patibility of the com­plexes was also assessed by evaluating the cytotoxicity of the com­plexes on cultured normal human fibro­blast cells (WS1) in vitro. The com­pounds were found to be nontoxic after 24 h of incubation at concentrations up to 25 mM.

Computing details

For all structures, data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(L-Prolinato-κ²N,O)[tris(2-aminoethyl)amine-κ⁴N,N',N'',N''']cobalt(III) diiodide monohydrate (mo_18ca_kb36_0m)

Crystal data

[Co(C5H8NO2)(C6H18N4)]I2·H2O	F(000) = 572
Mr = 591.11	Dx = 2.041 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 9.4554 (7) Å	Cell parameters from 9912 reflections
b = 9.9010 (8) Å	θ = 2.2–28.4°
c = 10.3668 (8) Å	µ = 4.12 mm^−1
β = 97.567 (1)°	T = 100 K
V = 962.07 (13) Å^3	Block, orange
Z = 2	0.26 × 0.21 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer	4559 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.043
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 28.4°, θmin = 2.0°
Tmin = 0.674, Tmax = 0.746	h = −12→12
15921 measured reflections	k = −13→13
4668 independent reflections	l = −13→13

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.022	w = 1/[σ^2(Fo^2) + (0.0195P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.053	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.95 e Å^−3
4668 reflections	Δρmin = −0.45 e Å^−3
239 parameters	Absolute structure: Flack x determined using 2010 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
8 restraints	Absolute structure parameter: 0.023 (15)
Primary atom site location: dual

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
I1	0.25477 (3)	0.69136 (12)	0.04372 (3)	0.01913 (8)
O1S	0.9222 (6)	0.2323 (6)	0.6765 (6)	0.0605 (15)
H1SA	0.846540	0.263012	0.628793	0.091*
H1SB	0.931851	0.283697	0.745184	0.091*
I2	0.80028 (10)	0.4136 (3)	0.3900 (3)	0.0260 (5)	0.890 (15)
Co1	0.27721 (6)	0.31438 (13)	0.32730 (6)	0.01016 (12)
O1	0.4162 (3)	0.1887 (4)	0.4065 (3)	0.0138 (6)
O2	0.5714 (3)	0.1519 (4)	0.5844 (3)	0.0189 (7)
N1	0.1355 (4)	0.4397 (4)	0.2459 (4)	0.0131 (8)
H1A	0.185 (4)	0.506 (3)	0.220 (4)	0.009 (9)*
H1B	0.070 (5)	0.458 (7)	0.296 (5)	0.034 (17)*
N2	0.2555 (3)	0.2167 (4)	0.1622 (3)	0.0136 (8)
N3	0.1272 (4)	0.1925 (5)	0.3757 (4)	0.0155 (7)
H3A	0.156 (5)	0.148 (5)	0.448 (3)	0.023 (15)*
H3B	0.049 (4)	0.234 (6)	0.393 (6)	0.031 (17)*
N4	0.4317 (3)	0.4121 (4)	0.2594 (4)	0.0131 (7)
H4A	0.501 (4)	0.407 (6)	0.324 (4)	0.027 (15)*
H4B	0.422 (6)	0.5002 (16)	0.255 (5)	0.019 (14)*
N5	0.3101 (3)	0.4133 (4)	0.4914 (3)	0.0116 (7)
H5	0.341 (5)	0.493 (2)	0.473 (5)	0.009 (9)*
C1	0.0502 (4)	0.3774 (5)	0.1320 (4)	0.0171 (9)
H1C	0.006866	0.448173	0.071964	0.020*
H1D	−0.027330	0.321926	0.160166	0.020*
C2	0.1501 (4)	0.2887 (5)	0.0637 (4)	0.0165 (9)
H2A	0.093332	0.221520	0.008257	0.020*
H2B	0.202078	0.345550	0.007006	0.020*
C3	0.3995 (4)	0.2141 (5)	0.1171 (4)	0.0165 (10)
H3C	0.390953	0.184659	0.025112	0.020*
H3D	0.462823	0.150079	0.170480	0.020*
C4	0.4607 (5)	0.3555 (5)	0.1307 (5)	0.0166 (9)
H4C	0.564790	0.352975	0.126964	0.020*
H4D	0.415798	0.413277	0.058789	0.020*
C5	0.0854 (5)	0.0906 (5)	0.2706 (5)	0.0181 (10)
H5A	−0.002009	0.120368	0.214611	0.022*
H5B	0.065994	0.002182	0.309380	0.022*
C6	0.2075 (5)	0.0782 (5)	0.1914 (5)	0.0184 (9)
H6A	0.286956	0.027277	0.240922	0.022*
H6B	0.176132	0.029026	0.109478	0.022*
C7	0.1960 (4)	0.4343 (6)	0.5786 (5)	0.0184 (10)
H7A	0.139278	0.516207	0.552599	0.022*
H7B	0.131096	0.355540	0.574585	0.022*
C8	0.2759 (5)	0.4502 (6)	0.7129 (5)	0.0249 (11)
H8A	0.213986	0.430573	0.780572	0.030*
H8B	0.315708	0.542366	0.726565	0.030*
C9	0.3951 (6)	0.3441 (6)	0.7135 (5)	0.0285 (12)
H9A	0.476836	0.365620	0.780197	0.034*
H9B	0.359490	0.252586	0.730351	0.034*
C10	0.4373 (4)	0.3541 (5)	0.5766 (4)	0.0148 (9)
H10	0.519181	0.418257	0.578532	0.018*
C11	0.4791 (4)	0.2219 (5)	0.5211 (4)	0.0130 (9)
I2A	0.8063 (8)	0.3711 (18)	0.4190 (13)	0.0144 (19)	0.110 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01560 (13)	0.02095 (15)	0.02032 (15)	−0.00198 (12)	0.00036 (10)	0.00777 (13)
O1S	0.061 (3)	0.044 (3)	0.082 (4)	0.006 (3)	0.029 (3)	0.017 (3)
I2	0.01049 (19)	0.0407 (11)	0.0272 (7)	−0.0023 (3)	0.0034 (2)	−0.0142 (8)
Co1	0.0086 (2)	0.0100 (3)	0.0117 (3)	−0.0004 (2)	0.00058 (19)	0.0002 (2)
O1	0.0137 (13)	0.0127 (14)	0.0146 (14)	0.0023 (13)	0.0001 (10)	0.0000 (14)
O2	0.0193 (15)	0.0171 (17)	0.0196 (17)	0.0034 (13)	−0.0004 (13)	−0.0002 (13)
N1	0.0108 (16)	0.0130 (19)	0.0157 (19)	0.0004 (14)	0.0026 (13)	0.0034 (15)
N2	0.0118 (15)	0.014 (2)	0.0138 (18)	−0.0006 (14)	−0.0007 (13)	0.0003 (14)
N3	0.0140 (15)	0.0156 (17)	0.0166 (18)	−0.0022 (18)	0.0003 (13)	0.0020 (18)
N4	0.0099 (15)	0.0142 (18)	0.0153 (18)	0.0014 (15)	0.0018 (13)	−0.0005 (16)
N5	0.0099 (14)	0.0122 (17)	0.0129 (17)	0.0024 (15)	0.0023 (12)	0.0008 (16)
C1	0.0118 (18)	0.021 (2)	0.018 (2)	0.0000 (17)	−0.0030 (16)	0.0014 (19)
C2	0.0140 (19)	0.022 (2)	0.012 (2)	0.0014 (18)	−0.0021 (15)	0.0008 (19)
C3	0.0155 (18)	0.020 (3)	0.014 (2)	0.0026 (18)	0.0036 (15)	−0.0029 (19)
C4	0.0144 (19)	0.020 (2)	0.016 (2)	−0.0009 (17)	0.0055 (16)	−0.0048 (18)
C5	0.018 (2)	0.014 (2)	0.020 (3)	−0.0054 (18)	−0.0022 (18)	−0.0014 (19)
C6	0.019 (2)	0.014 (2)	0.020 (2)	−0.0034 (18)	−0.0041 (17)	−0.0031 (19)
C7	0.0116 (19)	0.025 (3)	0.020 (2)	0.0055 (19)	0.0059 (17)	0.003 (2)
C8	0.026 (2)	0.034 (3)	0.014 (2)	0.009 (2)	0.0026 (18)	−0.005 (2)
C9	0.036 (3)	0.032 (3)	0.017 (3)	0.018 (2)	−0.001 (2)	−0.001 (2)
C10	0.0116 (18)	0.015 (2)	0.017 (2)	0.0020 (17)	−0.0011 (16)	−0.0001 (18)
C11	0.0113 (17)	0.012 (2)	0.015 (2)	−0.0005 (15)	0.0023 (15)	0.0013 (16)
I2A	0.0076 (14)	0.020 (4)	0.016 (3)	−0.0014 (17)	0.0000 (14)	0.005 (3)

Geometric parameters (Å, º)

O1S—H1SA	0.8697	C1—H1D	0.9900
O1S—H1SB	0.8699	C1—C2	1.529 (6)
Co1—O1	1.915 (3)	C2—H2A	0.9900
Co1—N1	1.937 (4)	C2—H2B	0.9900
Co1—N2	1.953 (4)	C3—H3C	0.9900
Co1—N3	1.977 (4)	C3—H3D	0.9900
Co1—N4	1.959 (4)	C3—C4	1.515 (7)
Co1—N5	1.952 (4)	C4—H4C	0.9900
O1—C11	1.299 (5)	C4—H4D	0.9900
O2—C11	1.234 (5)	C5—H5A	0.9900
N1—H1A	0.868 (14)	C5—H5B	0.9900
N1—H1B	0.877 (14)	C5—C6	1.507 (7)
N1—C1	1.474 (6)	C6—H6A	0.9900
N2—C2	1.509 (5)	C6—H6B	0.9900
N2—C3	1.497 (5)	C7—H7A	0.9900
N2—C6	1.489 (6)	C7—H7B	0.9900
N3—H3A	0.883 (14)	C7—C8	1.503 (6)
N3—H3B	0.882 (14)	C8—H8A	0.9900
N3—C5	1.500 (6)	C8—H8B	0.9900
N4—H4A	0.879 (14)	C8—C9	1.540 (7)
N4—H4B	0.877 (14)	C9—H9A	0.9900
N4—C4	1.505 (6)	C9—H9B	0.9900
N5—H5	0.875 (14)	C9—C10	1.527 (7)
N5—C7	1.510 (6)	C10—H10	1.0000
N5—C10	1.514 (5)	C10—C11	1.503 (6)
C1—H1C	0.9900
H1SA—O1S—H1SB	104.5	N2—C2—H2B	109.5
O1—Co1—N1	179.28 (15)	C1—C2—H2A	109.5
O1—Co1—N2	92.33 (14)	C1—C2—H2B	109.5
O1—Co1—N3	88.26 (15)	H2A—C2—H2B	108.1
O1—Co1—N4	88.43 (15)	N2—C3—H3C	110.1
O1—Co1—N5	86.04 (14)	N2—C3—H3D	110.1
N1—Co1—N2	87.05 (16)	N2—C3—C4	107.9 (4)
N1—Co1—N3	91.33 (16)	H3C—C3—H3D	108.4
N1—Co1—N4	91.89 (15)	C4—C3—H3C	110.1
N1—Co1—N5	94.59 (16)	C4—C3—H3D	110.1
N2—Co1—N3	85.65 (15)	N4—C4—C3	108.4 (4)
N2—Co1—N4	85.81 (15)	N4—C4—H4C	110.0
N4—Co1—N3	170.71 (17)	N4—C4—H4D	110.0
N5—Co1—N2	176.81 (14)	C3—C4—H4C	110.0
N5—Co1—N3	97.03 (16)	C3—C4—H4D	110.0
N5—Co1—N4	91.39 (15)	H4C—C4—H4D	108.4
C11—O1—Co1	115.6 (3)	N3—C5—H5A	110.2
Co1—N1—H1A	105 (3)	N3—C5—H5B	110.2
Co1—N1—H1B	112 (4)	N3—C5—C6	107.6 (4)
H1A—N1—H1B	118 (6)	H5A—C5—H5B	108.5
C1—N1—Co1	110.8 (3)	C6—C5—H5A	110.2
C1—N1—H1A	109 (3)	C6—C5—H5B	110.2
C1—N1—H1B	102 (4)	N2—C6—C5	108.2 (4)
C2—N2—Co1	110.0 (3)	N2—C6—H6A	110.1
C3—N2—Co1	106.7 (3)	N2—C6—H6B	110.1
C3—N2—C2	110.1 (3)	C5—C6—H6A	110.1
C6—N2—Co1	106.1 (3)	C5—C6—H6B	110.1
C6—N2—C2	112.4 (3)	H6A—C6—H6B	108.4
C6—N2—C3	111.3 (3)	N5—C7—H7A	110.8
Co1—N3—H3A	111 (4)	N5—C7—H7B	110.8
Co1—N3—H3B	114 (4)	H7A—C7—H7B	108.8
H3A—N3—H3B	104 (5)	C8—C7—N5	105.0 (4)
C5—N3—Co1	110.9 (3)	C8—C7—H7A	110.8
C5—N3—H3A	108 (4)	C8—C7—H7B	110.8
C5—N3—H3B	108 (4)	C7—C8—H8A	111.3
Co1—N4—H4A	102 (4)	C7—C8—H8B	111.3
Co1—N4—H4B	116 (4)	C7—C8—C9	102.1 (4)
H4A—N4—H4B	99 (5)	H8A—C8—H8B	109.2
C4—N4—Co1	111.5 (3)	C9—C8—H8A	111.3
C4—N4—H4A	117 (4)	C9—C8—H8B	111.3
C4—N4—H4B	110 (4)	C8—C9—H9A	111.1
Co1—N5—H5	107 (3)	C8—C9—H9B	111.1
C7—N5—Co1	123.1 (3)	H9A—C9—H9B	109.0
C7—N5—H5	107 (3)	C10—C9—C8	103.5 (4)
C7—N5—C10	106.2 (3)	C10—C9—H9A	111.1
C10—N5—Co1	109.7 (3)	C10—C9—H9B	111.1
C10—N5—H5	102 (3)	N5—C10—C9	106.4 (4)
N1—C1—H1C	110.2	N5—C10—H10	108.6
N1—C1—H1D	110.2	C9—C10—H10	108.6
N1—C1—C2	107.8 (3)	C11—C10—N5	110.0 (3)
H1C—C1—H1D	108.5	C11—C10—C9	114.4 (4)
C2—C1—H1C	110.2	C11—C10—H10	108.6
C2—C1—H1D	110.2	O1—C11—C10	117.3 (4)
N2—C2—C1	110.6 (4)	O2—C11—O1	123.4 (4)
N2—C2—H2A	109.5	O2—C11—C10	119.3 (4)
Co1—O1—C11—O2	−179.7 (3)	N5—C10—C11—O2	−172.6 (4)
Co1—O1—C11—C10	−0.8 (5)	C2—N2—C3—C4	72.5 (4)
Co1—N1—C1—C2	−37.3 (4)	C2—N2—C6—C5	−71.8 (4)
Co1—N2—C2—C1	−22.9 (4)	C3—N2—C2—C1	−140.3 (4)
Co1—N2—C3—C4	−46.9 (4)	C3—N2—C6—C5	164.2 (3)
Co1—N2—C6—C5	48.5 (4)	C6—N2—C2—C1	95.1 (4)
Co1—N3—C5—C6	22.5 (4)	C6—N2—C3—C4	−162.2 (4)
Co1—N4—C4—C3	−19.5 (4)	C7—N5—C10—C9	−1.0 (5)
Co1—N5—C7—C8	153.2 (3)	C7—N5—C10—C11	123.5 (4)
Co1—N5—C10—C9	−136.1 (3)	C7—C8—C9—C10	38.6 (5)
Co1—N5—C10—C11	−11.6 (4)	C8—C9—C10—N5	−23.2 (5)
N1—C1—C2—N2	38.9 (5)	C8—C9—C10—C11	−145.0 (4)
N2—C3—C4—N4	43.1 (5)	C9—C10—C11—O1	128.2 (4)
N3—C5—C6—N2	−46.3 (5)	C9—C10—C11—O2	−52.9 (6)
N5—C7—C8—C9	−39.8 (5)	C10—N5—C7—C8	25.7 (5)
N5—C10—C11—O1	8.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1S—H1SA···I2	0.87	2.87	3.532 (8)	134
O1S—H1SA···O2	0.87	2.81	3.422 (7)	129
N1—H1A···I1	0.87 (1)	2.73 (2)	3.535 (4)	155 (4)
N1—H1B···I2^i	0.88 (1)	2.88 (3)	3.687 (4)	153 (5)
N3—H3A···I2^ii	0.88 (1)	2.86 (3)	3.682 (4)	155 (5)
N3—H3B···I2^i	0.88 (1)	2.95 (2)	3.807 (5)	165 (5)
N4—H4A···I2	0.88 (1)	2.82 (4)	3.568 (4)	144 (5)
N4—H4B···I1	0.88 (1)	3.16 (4)	3.802 (4)	132 (4)
N4—H4B···O2^iii	0.88 (1)	2.24 (4)	2.876 (5)	129 (5)
N5—H5···O2^iii	0.88 (1)	1.91 (2)	2.772 (5)	170 (5)

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

(L-Asparaginato-κ²N,O)[tris(2-aminoethyl)amine-κ⁴N,N',N'',N''']cobalt(III) chloride perchlorate (mo_18ca_kb35_0ma)

Crystal data

[Co(C4H7N2O3)(C6H18N4)](Cl)(ClO4)	F(000) = 936
Mr = 452.18	Dx = 1.658 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.6098 (14) Å	Cell parameters from 9906 reflections
b = 11.1177 (11) Å	θ = 2.5–28.1°
c = 13.6429 (14) Å	µ = 1.28 mm^−1
β = 118.651 (2)°	T = 100 K
V = 1811.5 (3) Å^3	Plank, pink
Z = 4	0.28 × 0.24 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer	3897 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.047
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 28.3°, θmin = 2.5°
Tmin = 0.688, Tmax = 0.746	h = −18→18
36990 measured reflections	k = −14→14
4480 independent reflections	l = −18→17

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0513P)^2 + 1.9256P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
4480 reflections	Δρmax = 1.32 e Å^−3
250 parameters	Δρmin = −0.37 e Å^−3
6 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
Co1	0.28145 (2)	0.80081 (2)	0.46546 (2)	0.01229 (9)
O1	0.16440 (13)	0.86543 (14)	0.32794 (12)	0.0161 (3)
O2	0.11889 (13)	0.89305 (14)	0.14818 (13)	0.0188 (3)
N1	0.35135 (16)	0.95949 (16)	0.50444 (16)	0.0162 (4)
H1A	0.339 (2)	0.999 (2)	0.4444 (17)	0.025 (7)*
H1B	0.4237 (12)	0.955 (3)	0.549 (2)	0.026 (7)*
N2	0.34911 (15)	0.76140 (16)	0.37327 (15)	0.0142 (3)
N3	0.40068 (16)	0.72726 (16)	0.59985 (15)	0.0146 (3)
H3A	0.4619 (15)	0.719 (2)	0.595 (2)	0.013 (6)*
H3B	0.421 (2)	0.769 (2)	0.6615 (17)	0.027 (8)*
N4	0.20304 (16)	0.64738 (17)	0.44178 (15)	0.0161 (4)
H4	0.175 (2)	0.631 (2)	0.3703 (12)	0.019 (7)*
N5	0.19616 (16)	0.85177 (17)	0.53717 (15)	0.0167 (4)
H5	0.235 (2)	0.833 (3)	0.6080 (13)	0.026 (7)*
C1	0.3067 (2)	1.0291 (2)	0.5681 (2)	0.0219 (5)
H1C	0.305791	1.116050	0.552071	0.026*
H1D	0.354782	1.016557	0.649313	0.026*
C2	0.1894 (2)	0.9854 (2)	0.5325 (2)	0.0213 (5)
H2A	0.162767	1.016181	0.583756	0.026*
H2B	0.137352	1.012866	0.455807	0.026*
C3	0.36783 (19)	0.60397 (19)	0.61738 (18)	0.0171 (4)
H3C	0.330167	0.608123	0.663918	0.020*
H3D	0.434929	0.552260	0.655774	0.020*
C4	0.2888 (2)	0.55292 (19)	0.50314 (19)	0.0182 (4)
H4A	0.330295	0.532758	0.462371	0.022*
H4B	0.252455	0.478963	0.510696	0.022*
C5	0.11662 (19)	0.6556 (2)	0.48004 (19)	0.0202 (5)
H5A	0.146044	0.619237	0.555145	0.024*
H5B	0.048501	0.610870	0.427890	0.024*
C6	0.08801 (19)	0.7864 (2)	0.4839 (2)	0.0209 (5)
H6A	0.039468	0.817328	0.407504	0.025*
H6B	0.048375	0.796108	0.528151	0.025*
C7	0.18189 (18)	0.85643 (19)	0.24278 (18)	0.0155 (4)
C8	0.29091 (19)	0.79545 (19)	0.27156 (18)	0.0159 (4)
C9	0.3419 (2)	0.7716 (2)	0.19850 (19)	0.0197 (5)
H9A	0.369136	0.846595	0.180512	0.024*
H9B	0.288432	0.731186	0.128309	0.024*
C10	0.4394 (2)	0.6879 (2)	0.2734 (2)	0.0284 (6)
H10A	0.420311	0.602971	0.250317	0.034*
H10B	0.508047	0.709371	0.269563	0.034*
C11	0.45594 (19)	0.7076 (2)	0.39169 (19)	0.0196 (4)
H11A	0.470162	0.630449	0.432459	0.024*
H11B	0.519366	0.762852	0.434625	0.024*
Cl1	0.10831 (5)	0.57484 (5)	0.18753 (4)	0.02043 (13)
Cl2	0.22314 (5)	0.30432 (5)	0.68077 (5)	0.02044 (13)
O3	0.17091 (17)	0.29218 (17)	0.56145 (15)	0.0308 (4)
O4	0.30373 (18)	0.40045 (19)	0.71921 (17)	0.0384 (5)
O5	0.2812 (2)	0.19463 (18)	0.73485 (18)	0.0421 (5)
O6	0.14047 (16)	0.3274 (2)	0.71582 (16)	0.0340 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.01261 (15)	0.01375 (15)	0.01002 (15)	−0.00012 (10)	0.00503 (12)	0.00058 (10)
O1	0.0150 (7)	0.0196 (7)	0.0130 (7)	0.0017 (6)	0.0063 (6)	0.0024 (6)
O2	0.0164 (8)	0.0240 (8)	0.0118 (7)	−0.0002 (6)	0.0033 (6)	0.0046 (6)
N1	0.0177 (9)	0.0148 (8)	0.0138 (9)	−0.0010 (7)	0.0057 (8)	0.0008 (7)
N2	0.0144 (9)	0.0145 (8)	0.0137 (8)	−0.0008 (7)	0.0066 (7)	−0.0003 (7)
N3	0.0158 (9)	0.0156 (8)	0.0125 (8)	0.0001 (7)	0.0069 (7)	−0.0002 (7)
N4	0.0175 (9)	0.0182 (9)	0.0115 (8)	−0.0024 (7)	0.0060 (7)	−0.0007 (7)
N5	0.0152 (9)	0.0204 (9)	0.0144 (9)	0.0012 (7)	0.0070 (8)	0.0021 (7)
C1	0.0280 (12)	0.0171 (10)	0.0206 (11)	0.0004 (9)	0.0116 (10)	−0.0023 (9)
C2	0.0240 (12)	0.0197 (11)	0.0217 (11)	0.0046 (9)	0.0122 (10)	−0.0016 (9)
C3	0.0176 (10)	0.0148 (9)	0.0173 (10)	0.0005 (8)	0.0072 (9)	0.0036 (8)
C4	0.0228 (11)	0.0138 (9)	0.0195 (11)	−0.0012 (8)	0.0113 (9)	−0.0014 (8)
C5	0.0155 (10)	0.0258 (11)	0.0186 (11)	−0.0032 (9)	0.0076 (9)	0.0021 (9)
C6	0.0140 (10)	0.0286 (12)	0.0197 (11)	−0.0005 (9)	0.0077 (9)	0.0014 (9)
C7	0.0153 (10)	0.0155 (9)	0.0151 (10)	−0.0034 (8)	0.0067 (8)	−0.0002 (8)
C8	0.0173 (10)	0.0155 (9)	0.0161 (10)	−0.0019 (8)	0.0089 (9)	0.0004 (8)
C9	0.0241 (12)	0.0227 (11)	0.0156 (10)	0.0024 (9)	0.0120 (10)	0.0012 (8)
C10	0.0303 (14)	0.0357 (14)	0.0239 (13)	0.0123 (11)	0.0166 (11)	0.0038 (10)
C11	0.0169 (11)	0.0243 (11)	0.0178 (11)	0.0059 (9)	0.0084 (9)	0.0032 (9)
Cl1	0.0203 (3)	0.0207 (3)	0.0157 (3)	0.0035 (2)	0.0049 (2)	−0.00386 (19)
Cl2	0.0263 (3)	0.0207 (3)	0.0186 (3)	−0.0043 (2)	0.0143 (2)	−0.00254 (19)
O3	0.0396 (11)	0.0370 (10)	0.0187 (9)	−0.0037 (8)	0.0163 (8)	−0.0004 (7)
O4	0.0423 (12)	0.0407 (11)	0.0360 (11)	−0.0194 (9)	0.0218 (10)	−0.0067 (9)
O5	0.0657 (16)	0.0306 (11)	0.0323 (11)	0.0149 (10)	0.0253 (11)	0.0077 (8)
O6	0.0237 (9)	0.0581 (13)	0.0228 (9)	−0.0011 (9)	0.0131 (8)	−0.0003 (9)

Geometric parameters (Å, º)

Co1—O1	1.9256 (15)	C2—H2B	0.9900
Co1—N1	1.9533 (19)	C3—H3C	0.9900
Co1—N2	1.9321 (18)	C3—H3D	0.9900
Co1—N3	1.9520 (19)	C3—C4	1.517 (3)
Co1—N4	1.9550 (19)	C4—H4A	0.9900
Co1—N5	1.9273 (19)	C4—H4B	0.9900
O1—C7	1.297 (3)	C5—H5A	0.9900
O2—C7	1.227 (3)	C5—H5B	0.9900
N1—H1A	0.870 (14)	C5—C6	1.513 (3)
N1—H1B	0.875 (14)	C6—H6A	0.9900
N1—C1	1.492 (3)	C6—H6B	0.9900
N2—C8	1.282 (3)	C7—C8	1.502 (3)
N2—C11	1.478 (3)	C8—C9	1.486 (3)
N3—H3A	0.874 (13)	C9—H9A	0.9900
N3—H3B	0.883 (14)	C9—H9B	0.9900
N3—C3	1.496 (3)	C9—C10	1.540 (3)
N4—H4	0.879 (14)	C10—H10A	0.9900
N4—C4	1.493 (3)	C10—H10B	0.9900
N4—C5	1.501 (3)	C10—C11	1.535 (3)
N5—H5	0.876 (14)	C11—H11A	0.9900
N5—C2	1.488 (3)	C11—H11B	0.9900
N5—C6	1.482 (3)	Cl2—O3	1.4366 (19)
C1—H1C	0.9900	Cl2—O4	1.438 (2)
C1—H1D	0.9900	Cl2—O5	1.448 (2)
C1—C2	1.509 (3)	Cl2—O6	1.4409 (19)
C2—H2A	0.9900
O1—Co1—N1	89.75 (7)	N3—C3—H3C	110.3
O1—Co1—N2	83.12 (7)	N3—C3—H3D	110.3
O1—Co1—N3	176.62 (7)	N3—C3—C4	107.31 (17)
O1—Co1—N4	91.92 (7)	H3C—C3—H3D	108.5
O1—Co1—N5	88.09 (7)	C4—C3—H3C	110.3
N1—Co1—N4	171.52 (8)	C4—C3—H3D	110.3
N2—Co1—N1	93.44 (8)	N4—C4—C3	106.95 (17)
N2—Co1—N3	94.32 (8)	N4—C4—H4A	110.3
N2—Co1—N4	95.01 (8)	N4—C4—H4B	110.3
N3—Co1—N1	92.61 (8)	C3—C4—H4A	110.3
N3—Co1—N4	86.09 (8)	C3—C4—H4B	110.3
N5—Co1—N1	85.96 (8)	H4A—C4—H4B	108.6
N5—Co1—N2	171.19 (8)	N4—C5—H5A	109.9
N5—Co1—N3	94.48 (8)	N4—C5—H5B	109.9
N5—Co1—N4	85.79 (8)	N4—C5—C6	109.14 (18)
C7—O1—Co1	115.01 (14)	H5A—C5—H5B	108.3
Co1—N1—H1A	110 (2)	C6—C5—H5A	109.9
Co1—N1—H1B	111.9 (19)	C6—C5—H5B	109.9
H1A—N1—H1B	109 (3)	N5—C6—C5	106.07 (18)
C1—N1—Co1	110.22 (14)	N5—C6—H6A	110.5
C1—N1—H1A	109.8 (19)	N5—C6—H6B	110.5
C1—N1—H1B	105.5 (19)	C5—C6—H6A	110.5
C8—N2—Co1	113.44 (15)	C5—C6—H6B	110.5
C8—N2—C11	110.52 (18)	H6A—C6—H6B	108.7
C11—N2—Co1	135.91 (15)	O1—C7—C8	112.53 (18)
Co1—N3—H3A	111.3 (17)	O2—C7—O1	125.5 (2)
Co1—N3—H3B	114.4 (19)	O2—C7—C8	122.0 (2)
H3A—N3—H3B	105 (3)	N2—C8—C7	115.89 (19)
C3—N3—Co1	110.88 (14)	N2—C8—C9	115.4 (2)
C3—N3—H3A	106.6 (17)	C9—C8—C7	128.71 (19)
C3—N3—H3B	108.4 (19)	C8—C9—H9A	111.5
Co1—N4—H4	105.9 (18)	C8—C9—H9B	111.5
C4—N4—Co1	107.64 (13)	C8—C9—C10	101.16 (18)
C4—N4—H4	106.5 (18)	H9A—C9—H9B	109.4
C4—N4—C5	112.33 (17)	C10—C9—H9A	111.5
C5—N4—Co1	110.26 (14)	C10—C9—H9B	111.5
C5—N4—H4	113.8 (18)	C9—C10—H10A	110.8
Co1—N5—H5	107 (2)	C9—C10—H10B	110.8
C2—N5—Co1	108.17 (14)	H10A—C10—H10B	108.8
C2—N5—H5	106 (2)	C11—C10—C9	104.89 (19)
C6—N5—Co1	107.75 (14)	C11—C10—H10A	110.8
C6—N5—H5	111 (2)	C11—C10—H10B	110.8
C6—N5—C2	116.25 (18)	N2—C11—C10	104.03 (18)
N1—C1—H1C	110.1	N2—C11—H11A	111.0
N1—C1—H1D	110.1	N2—C11—H11B	111.0
N1—C1—C2	108.01 (18)	C10—C11—H11A	111.0
H1C—C1—H1D	108.4	C10—C11—H11B	111.0
C2—C1—H1C	110.1	H11A—C11—H11B	109.0
C2—C1—H1D	110.1	O3—Cl2—O4	111.07 (12)
N5—C2—C1	105.88 (19)	O3—Cl2—O5	110.54 (12)
N5—C2—H2A	110.6	O3—Cl2—O6	110.61 (12)
N5—C2—H2B	110.6	O4—Cl2—O5	107.78 (14)
C1—C2—H2A	110.6	O4—Cl2—O6	109.09 (13)
C1—C2—H2B	110.6	O6—Cl2—O5	107.64 (13)
H2A—C2—H2B	108.7
Co1—O1—C7—O2	−179.03 (17)	N1—C1—C2—N5	48.1 (2)
Co1—O1—C7—C8	0.6 (2)	N2—C8—C9—C10	11.5 (3)
Co1—N1—C1—C2	−28.1 (2)	N3—C3—C4—N4	−48.3 (2)
Co1—N2—C8—C7	−1.1 (2)	N4—C5—C6—N5	−44.3 (2)
Co1—N2—C8—C9	177.56 (15)	C2—N5—C6—C5	169.55 (18)
Co1—N2—C11—C10	171.36 (17)	C4—N4—C5—C6	140.80 (19)
Co1—N3—C3—C4	29.7 (2)	C5—N4—C4—C3	−76.8 (2)
Co1—N4—C4—C3	44.81 (19)	C6—N5—C2—C1	−167.78 (18)
Co1—N4—C5—C6	20.7 (2)	C7—C8—C9—C10	−170.1 (2)
Co1—N5—C2—C1	−46.5 (2)	C8—N2—C11—C10	−13.2 (2)
Co1—N5—C6—C5	48.02 (19)	C8—C9—C10—C11	−18.3 (2)
O1—C7—C8—N2	0.4 (3)	C9—C10—C11—N2	19.4 (3)
O1—C7—C8—C9	−178.1 (2)	C11—N2—C8—C7	−177.62 (18)
O2—C7—C8—N2	180.0 (2)	C11—N2—C8—C9	1.0 (3)
O2—C7—C8—C9	1.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1^i	0.87 (1)	2.39 (2)	3.191 (2)	153 (3)
N1—H1B···Cl1^ii	0.88 (1)	2.33 (2)	3.200 (2)	170 (3)
N3—H3A···O2^ii	0.87 (1)	2.27 (2)	3.028 (2)	145 (2)
N3—H3B···O6^iii	0.88 (1)	2.29 (2)	3.038 (3)	142 (3)
N4—H4···Cl1	0.88 (1)	2.29 (1)	3.1712 (19)	176 (2)
N5—H5···Cl2^iii	0.88 (1)	2.68 (2)	3.4985 (19)	157 (3)
N5—H5···O4^iii	0.88 (1)	2.75 (2)	3.367 (3)	128 (2)
N5—H5···O5^iii	0.88 (1)	2.73 (2)	3.450 (3)	140 (2)
N5—H5···O6^iii	0.88 (1)	2.18 (2)	3.031 (3)	164 (3)
C5—H5B···O6^iv	0.99	2.47	3.233 (3)	134

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x+1/2, −y+3/2, z+1/2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) −x, −y+1, −z+1.

(L-Prolinato-κ²N,O)(triethylenetetramine-κ⁴N,N',N'',N''')cobalt(III) chloride perchlorate (mo_17ca3_charm_kb15_0m)

Crystal data

[Co(C4H7N2O3)(C6H18N4)](Cl)(ClO4)	Dx = 1.797 Mg m^−3
Mr = 471.19	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 6780 reflections
a = 11.5455 (6) Å	θ = 2.9–27.1°
b = 11.8865 (6) Å	µ = 1.34 mm^−1
c = 25.3868 (12) Å	T = 173 K
V = 3484.0 (3) Å^3	Plate, clear light orange
Z = 8	0.16 × 0.15 × 0.08 mm
F(000) = 1952

Data collection

Bruker APEXII CCD diffractometer	2936 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.095
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 28.3°, θmin = 2.9°
Tmin = 0.683, Tmax = 0.746	h = −15→13
30905 measured reflections	k = −14→15
4317 independent reflections	l = −33→33

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0275P)^2 + 5.0627P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
4317 reflections	Δρmax = 0.47 e Å^−3
275 parameters	Δρmin = −0.49 e Å^−3
10 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
Co1	0.44983 (3)	0.52347 (3)	0.61513 (2)	0.00972 (11)
Cl1	0.30771 (7)	0.23485 (6)	0.69372 (3)	0.02074 (19)
O1	0.35842 (17)	0.49365 (16)	0.55504 (8)	0.0137 (5)
O2	0.24613 (19)	0.57093 (18)	0.49382 (8)	0.0201 (5)
O3	0.47724 (19)	0.71487 (18)	0.49385 (8)	0.0197 (5)
N1	0.5548 (2)	0.5465 (2)	0.67400 (9)	0.0122 (5)
N2	0.3274 (2)	0.4991 (2)	0.66746 (9)	0.0118 (6)
N3	0.4946 (2)	0.3660 (2)	0.61680 (10)	0.0145 (6)
N4	0.5815 (2)	0.5622 (2)	0.57012 (10)	0.0147 (6)
N5	0.3942 (2)	0.6797 (2)	0.60810 (10)	0.0115 (5)
N6	0.4264 (3)	0.8941 (2)	0.47622 (11)	0.0200 (6)
C1	0.4824 (3)	0.5864 (3)	0.71934 (11)	0.0146 (7)
H1A	0.460451	0.666167	0.714163	0.017*
H1B	0.526720	0.580283	0.752611	0.017*
C2	0.3755 (3)	0.5138 (3)	0.72190 (11)	0.0156 (7)
H2C	0.395214	0.439448	0.737024	0.019*
H2D	0.316798	0.549631	0.744854	0.019*
C3	0.6132 (3)	0.4361 (3)	0.68762 (12)	0.0185 (7)
H3C	0.694624	0.450471	0.697877	0.022*
H3D	0.573283	0.401162	0.718008	0.022*
C4	0.6105 (3)	0.3560 (3)	0.64122 (13)	0.0206 (8)
H4C	0.671464	0.376136	0.615467	0.025*
H4D	0.623997	0.277854	0.653222	0.025*
C5	0.6388 (3)	0.6341 (3)	0.65707 (12)	0.0167 (7)
H5C	0.705319	0.635940	0.681674	0.020*
H5D	0.601187	0.708891	0.657460	0.020*
C6	0.6808 (3)	0.6070 (3)	0.60185 (12)	0.0215 (8)
H6C	0.712026	0.675742	0.585025	0.026*
H6D	0.743502	0.550274	0.603456	0.026*
C7	0.3005 (3)	0.6837 (2)	0.56767 (11)	0.0117 (6)
H7	0.225338	0.685183	0.587205	0.014*
C8	0.3015 (3)	0.5760 (3)	0.53548 (12)	0.0141 (7)
C9	0.3044 (3)	0.7889 (2)	0.53433 (11)	0.0143 (7)
H9A	0.301917	0.855404	0.557747	0.017*
H9B	0.234644	0.791079	0.511652	0.017*
C10	0.4109 (3)	0.7963 (3)	0.49989 (11)	0.0141 (7)
Cl2	0.49681 (7)	0.04021 (6)	0.36275 (3)	0.01618 (17)
O4	0.5877 (2)	−0.0123 (2)	0.39285 (9)	0.0274 (6)
O5	0.4346 (2)	0.11693 (19)	0.39676 (9)	0.0262 (6)
O6	0.5473 (2)	0.1021 (2)	0.31989 (9)	0.0306 (6)
O7	0.4191 (2)	−0.0437 (2)	0.34315 (9)	0.0276 (6)
H2A	0.272 (2)	0.549 (2)	0.6632 (12)	0.013 (9)*
H2B	0.295 (3)	0.4323 (17)	0.6652 (14)	0.033 (11)*
H3A	0.491 (3)	0.342 (3)	0.5844 (7)	0.025 (10)*
H3B	0.444 (2)	0.324 (2)	0.6340 (12)	0.022 (10)*
H4A	0.556 (3)	0.611 (2)	0.5470 (10)	0.014 (9)*
H4B	0.600 (3)	0.503 (2)	0.5505 (12)	0.029 (10)*
H5A	0.363 (2)	0.704 (2)	0.6379 (8)	0.011 (8)*
H5B	0.4519 (19)	0.725 (2)	0.6003 (11)	0.011 (8)*
H6A	0.381 (3)	0.951 (2)	0.4826 (14)	0.033 (11)*
H6B	0.490 (2)	0.900 (3)	0.4583 (12)	0.030 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0094 (2)	0.01083 (19)	0.00894 (19)	0.00124 (18)	−0.00032 (17)	−0.00128 (17)
Cl1	0.0243 (4)	0.0144 (4)	0.0235 (4)	−0.0042 (4)	−0.0087 (4)	0.0024 (3)
O1	0.0151 (11)	0.0113 (11)	0.0148 (11)	0.0022 (9)	−0.0033 (9)	−0.0022 (9)
O2	0.0226 (13)	0.0206 (12)	0.0170 (12)	0.0017 (10)	−0.0084 (10)	−0.0032 (10)
O3	0.0227 (14)	0.0177 (12)	0.0186 (12)	0.0075 (10)	0.0065 (10)	0.0029 (10)
N1	0.0135 (13)	0.0142 (14)	0.0087 (12)	0.0007 (12)	−0.0006 (10)	0.0003 (10)
N2	0.0105 (14)	0.0133 (15)	0.0116 (13)	0.0006 (12)	0.0004 (11)	0.0003 (11)
N3	0.0168 (14)	0.0128 (13)	0.0138 (14)	0.0033 (12)	−0.0014 (13)	−0.0035 (12)
N4	0.0131 (14)	0.0208 (15)	0.0103 (13)	0.0017 (12)	0.0005 (11)	0.0006 (12)
N5	0.0142 (14)	0.0112 (13)	0.0092 (13)	−0.0021 (11)	0.0013 (11)	−0.0002 (11)
N6	0.0194 (17)	0.0198 (16)	0.0207 (16)	0.0031 (13)	0.0041 (13)	0.0037 (13)
C1	0.0204 (18)	0.0156 (16)	0.0078 (14)	0.0003 (14)	0.0002 (13)	−0.0013 (12)
C2	0.0151 (17)	0.0198 (17)	0.0117 (15)	−0.0003 (14)	0.0011 (12)	−0.0025 (13)
C3	0.0181 (18)	0.0216 (18)	0.0158 (17)	0.0044 (15)	−0.0056 (14)	0.0005 (13)
C4	0.0190 (18)	0.0222 (18)	0.0206 (18)	0.0086 (15)	−0.0044 (15)	−0.0005 (14)
C5	0.0108 (16)	0.0243 (18)	0.0151 (16)	−0.0062 (15)	−0.0039 (13)	0.0045 (14)
C6	0.0101 (17)	0.039 (2)	0.0154 (17)	−0.0045 (15)	−0.0003 (13)	0.0019 (15)
C7	0.0097 (15)	0.0151 (16)	0.0103 (15)	0.0023 (13)	−0.0021 (13)	−0.0002 (12)
C8	0.0105 (16)	0.0169 (16)	0.0151 (16)	−0.0013 (14)	0.0011 (13)	−0.0011 (13)
C9	0.0198 (17)	0.0129 (16)	0.0100 (15)	0.0044 (14)	0.0001 (13)	−0.0009 (12)
C10	0.0202 (18)	0.0150 (16)	0.0072 (15)	−0.0026 (15)	−0.0046 (13)	−0.0006 (13)
Cl2	0.0164 (4)	0.0199 (4)	0.0123 (3)	−0.0049 (3)	0.0029 (3)	−0.0001 (3)
O4	0.0195 (12)	0.0383 (15)	0.0243 (13)	0.0049 (11)	−0.0029 (10)	0.0017 (11)
O5	0.0295 (14)	0.0243 (13)	0.0249 (13)	0.0055 (11)	0.0117 (11)	−0.0004 (10)
O6	0.0388 (15)	0.0343 (14)	0.0186 (12)	−0.0192 (13)	0.0093 (11)	0.0050 (11)
O7	0.0260 (13)	0.0328 (15)	0.0239 (13)	−0.0179 (12)	0.0002 (10)	−0.0050 (11)

Geometric parameters (Å, º)

Co1—O1	1.889 (2)	N6—H6B	0.871 (14)
Co1—N1	1.943 (2)	C1—H1A	0.9900
Co1—N2	1.961 (3)	C1—H1B	0.9900
Co1—N3	1.942 (3)	C1—C2	1.508 (4)
Co1—N4	1.957 (3)	C2—H2C	0.9900
Co1—N5	1.973 (3)	C2—H2D	0.9900
O1—C8	1.280 (3)	C3—H3C	0.9900
O2—C8	1.237 (3)	C3—H3D	0.9900
O3—C10	1.243 (3)	C3—C4	1.515 (4)
N1—C1	1.499 (4)	C4—H4C	0.9900
N1—C3	1.516 (4)	C4—H4D	0.9900
N1—C5	1.487 (4)	C5—H5C	0.9900
N2—C2	1.499 (4)	C5—H5D	0.9900
N2—H2A	0.884 (14)	C5—C6	1.518 (4)
N2—H2B	0.879 (14)	C6—H6C	0.9900
N3—C4	1.480 (4)	C6—H6D	0.9900
N3—H3A	0.871 (14)	C7—H7	1.0000
N3—H3B	0.881 (14)	C7—C8	1.518 (4)
N4—C6	1.499 (4)	C7—C9	1.511 (4)
N4—H4A	0.877 (14)	C9—H9A	0.9900
N4—H4B	0.886 (14)	C9—H9B	0.9900
N5—C7	1.492 (4)	C9—C10	1.512 (4)
N5—H5A	0.885 (14)	Cl2—O4	1.441 (2)
N5—H5B	0.880 (14)	Cl2—O5	1.447 (2)
N6—C10	1.321 (4)	Cl2—O6	1.437 (2)
N6—H6A	0.875 (14)	Cl2—O7	1.431 (2)
O1—Co1—N1	174.92 (10)	N2—C2—C1	109.3 (2)
O1—Co1—N2	96.70 (10)	N2—C2—H2C	109.8
O1—Co1—N3	89.17 (10)	N2—C2—H2D	109.8
O1—Co1—N4	90.38 (10)	C1—C2—H2C	109.8
O1—Co1—N5	85.50 (9)	C1—C2—H2D	109.8
N1—Co1—N2	87.08 (10)	H2C—C2—H2D	108.3
N1—Co1—N4	86.08 (11)	N1—C3—H3C	109.5
N1—Co1—N5	98.06 (10)	N1—C3—H3D	109.5
N2—Co1—N5	88.01 (11)	H3C—C3—H3D	108.0
N3—Co1—N1	87.30 (11)	C4—C3—N1	110.9 (2)
N3—Co1—N2	92.00 (11)	C4—C3—H3C	109.5
N3—Co1—N4	91.89 (12)	C4—C3—H3D	109.5
N3—Co1—N5	174.63 (11)	N3—C4—C3	107.1 (3)
N4—Co1—N2	171.97 (11)	N3—C4—H4C	110.3
N4—Co1—N5	88.77 (11)	N3—C4—H4D	110.3
C8—O1—Co1	117.19 (18)	C3—C4—H4C	110.3
C1—N1—Co1	106.73 (18)	C3—C4—H4D	110.3
C1—N1—C3	110.3 (2)	H4C—C4—H4D	108.5
C3—N1—Co1	109.35 (17)	N1—C5—H5C	109.9
C5—N1—Co1	106.46 (17)	N1—C5—H5D	109.9
C5—N1—C1	111.3 (2)	N1—C5—C6	109.1 (2)
C5—N1—C3	112.4 (2)	H5C—C5—H5D	108.3
Co1—N2—H2A	110 (2)	C6—C5—H5C	109.9
Co1—N2—H2B	113 (2)	C6—C5—H5D	109.9
C2—N2—Co1	109.90 (18)	N4—C6—C5	109.1 (2)
C2—N2—H2A	108 (2)	N4—C6—H6C	109.9
C2—N2—H2B	109 (2)	N4—C6—H6D	109.9
H2A—N2—H2B	107 (3)	C5—C6—H6C	109.9
Co1—N3—H3A	107 (2)	C5—C6—H6D	109.9
Co1—N3—H3B	112 (2)	H6C—C6—H6D	108.3
C4—N3—Co1	109.1 (2)	N5—C7—H7	106.8
C4—N3—H3A	114 (2)	N5—C7—C8	109.8 (2)
C4—N3—H3B	110 (2)	N5—C7—C9	113.0 (2)
H3A—N3—H3B	105 (3)	C8—C7—H7	106.8
Co1—N4—H4A	107 (2)	C9—C7—H7	106.8
Co1—N4—H4B	109 (2)	C9—C7—C8	113.3 (2)
C6—N4—Co1	111.35 (19)	O1—C8—C7	116.1 (3)
C6—N4—H4A	112 (2)	O2—C8—O1	124.0 (3)
C6—N4—H4B	113 (2)	O2—C8—C7	119.8 (3)
H4A—N4—H4B	103 (3)	C7—C9—H9A	108.9
Co1—N5—H5A	111.3 (19)	C7—C9—H9B	108.9
Co1—N5—H5B	111 (2)	C7—C9—C10	113.3 (3)
C7—N5—Co1	109.17 (18)	H9A—C9—H9B	107.7
C7—N5—H5A	107 (2)	C10—C9—H9A	108.9
C7—N5—H5B	112 (2)	C10—C9—H9B	108.9
H5A—N5—H5B	107 (3)	O3—C10—N6	123.0 (3)
C10—N6—H6A	121 (2)	O3—C10—C9	121.8 (3)
C10—N6—H6B	115 (2)	N6—C10—C9	115.1 (3)
H6A—N6—H6B	123 (3)	O4—Cl2—O5	108.56 (14)
N1—C1—H1A	110.1	O6—Cl2—O4	109.17 (15)
N1—C1—H1B	110.1	O6—Cl2—O5	109.30 (14)
N1—C1—C2	107.9 (2)	O7—Cl2—O4	109.81 (15)
H1A—C1—H1B	108.4	O7—Cl2—O5	109.61 (14)
C2—C1—H1A	110.1	O7—Cl2—O6	110.37 (14)
C2—C1—H1B	110.1
Co1—O1—C8—O2	173.7 (2)	N5—Co1—O1—C8	−0.6 (2)
Co1—O1—C8—C7	−8.6 (3)	N5—C7—C8—O1	16.0 (4)
Co1—N1—C1—C2	44.8 (3)	N5—C7—C8—O2	−166.2 (3)
Co1—N1—C3—C4	21.9 (3)	N5—C7—C9—C10	65.9 (3)
Co1—N1—C5—C6	−45.6 (3)	C1—N1—C3—C4	138.9 (3)
Co1—N2—C2—C1	23.2 (3)	C1—N1—C5—C6	−161.6 (2)
Co1—N3—C4—C3	41.2 (3)	C3—N1—C1—C2	−73.9 (3)
Co1—N4—C6—C5	−13.2 (3)	C3—N1—C5—C6	74.1 (3)
Co1—N5—C7—C8	−15.2 (3)	C5—N1—C1—C2	160.6 (2)
Co1—N5—C7—C9	−142.7 (2)	C5—N1—C3—C4	−96.2 (3)
N1—C1—C2—N2	−44.6 (3)	C7—C9—C10—O3	11.1 (4)
N1—C3—C4—N3	−41.0 (3)	C7—C9—C10—N6	−170.2 (3)
N1—C5—C6—N4	38.4 (3)	C8—C7—C9—C10	−59.7 (3)
N2—Co1—O1—C8	86.9 (2)	C9—C7—C8—O1	143.3 (3)
N3—Co1—O1—C8	178.8 (2)	C9—C7—C8—O2	−38.9 (4)
N4—Co1—O1—C8	−89.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1^i	0.88 (1)	2.51 (2)	3.275 (3)	145 (3)
N2—H2A···O4^ii	0.88 (1)	2.59 (3)	3.167 (3)	123 (2)
N2—H2B···Cl1	0.88 (1)	2.46 (2)	3.219 (3)	145 (3)
N2—H2B···O6^ii	0.88 (1)	2.91 (3)	3.465 (4)	122 (3)
N3—H3A···O3^iii	0.87 (1)	2.13 (2)	2.987 (3)	168 (3)
N3—H3B···Cl1	0.88 (1)	2.43 (2)	3.301 (3)	170 (3)
N4—H4A···O3	0.88 (1)	2.04 (2)	2.914 (3)	172 (3)
N4—H4B···O1^iii	0.89 (1)	2.72 (3)	3.319 (3)	126 (3)
N4—H4B···O2^iii	0.89 (1)	2.28 (3)	3.017 (3)	141 (3)
N5—H5A···Cl1^i	0.89 (1)	2.46 (2)	3.254 (3)	150 (3)
N5—H5B···O5^iii	0.88 (1)	2.29 (2)	3.126 (3)	158 (3)
N6—H6A···O2^i	0.88 (1)	2.06 (2)	2.930 (4)	171 (3)
N6—H6B···Cl2^iv	0.87 (1)	2.94 (3)	3.461 (3)	120 (3)
N6—H6B···O4^iv	0.87 (1)	2.26 (2)	3.030 (4)	148 (3)

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