Tris(ethyl­enedi­amine)­cobalt(II) dichloride

Cooke, K.; Olenev, A.V.; Kovnir, K.

doi:10.1107/S1600536813013135

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page m332

doi:10.1107/S1600536813013135

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Tris(ethylenediamine)cobalt(II) dichloride

Kristin Cooke,^a Andrei V. Olenev ^a and Kirill Kovnir ^a ^*

^aDepartment of Chemistry, University of California, Davis, One Shields Ave, Davis, CA 95616, USA
^*Correspondence e-mail: kkovnir@ucdavis.edu

(Received 6 May 2013; accepted 13 May 2013; online 18 May 2013)

The title compound, [Co^II(C₂H₈N₂)₃]Cl₂, was obtained unexpectedly as the product of an attempted solvothermal synthesis of cobalt selenide from the elements in the presence of NH₄Cl in ethylenediamine solvent. The three chelate rings of the distorted octahedral [Co(C₂H₈N₂)₃]²⁺ complex cation adopt twisted conformations about their C—C bonds. The spread of cis-N—Co—N bond angles [80.17 (6)–98.10 (6)°] in the title compound is considerably greater than the equivalent data for [Co^III(C₂H₈N₂)₃]Cl₃ [Takamizawa et al. (2008 ). Angew. Chem. Int. Ed. 47, 1689–1692]. In the crystal, the components are linked by numerous N—H⋯Cl hydrogen bonds, generating a three-dimensional network in which the cationic complexes are stacked in columns along [010] and separated by columns of chloride anions.

Related literature

The corresponding Co^III–tris-ethylenediamine complex with chloride counter-anions has been reported by Takamizawa et al. (2008).

Experimental

Crystal data

[Co(C₂H₈N₂)₃]Cl₂
M_r = 310.14
Orthorhombic, P b c a
a = 8.1590 (8) Å
b = 17.047 (3) Å
c = 20.3974 (14) Å
V = 2837.0 (6) Å³
Z = 8
Cu Kα radiation
μ = 12.81 mm⁻¹
T = 90 K
0.31 × 0.17 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.109, T_max = 0.243
17930 measured reflections
2700 independent reflections
2437 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.059
S = 1.06
2700 reflections
232 parameters
All H-atom parameters refined
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected bond lengths (Å)

Co—N1	2.1540 (15)
Co—N3	2.1558 (15)
Co—N2	2.1635 (15)
Co—N5	2.1748 (15)
Co—N4	2.1767 (15)
Co—N6	2.1791 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯Cl2	0.82 (2)	2.48 (3)	3.2839 (17)	167 (2)
N1—H1A⋯Cl2ⁱ	0.86 (2)	2.57 (2)	3.3056 (16)	145.4 (18)
N2—H2A⋯Cl1ⁱⁱ	0.83 (2)	2.92 (2)	3.5494 (16)	133.6 (17)
N2—H2A⋯Cl2ⁱⁱⁱ	0.83 (2)	2.94 (2)	3.5887 (17)	135.8 (17)
N2—H2B⋯Cl1	0.88 (2)	2.65 (2)	3.4566 (17)	152.5 (18)
N5—H5B⋯Cl1ⁱⁱ	0.87 (2)	2.51 (2)	3.3770 (16)	173.1 (19)
N5—H5A⋯Cl1^iv	0.82 (2)	2.70 (2)	3.4514 (18)	152.4 (19)
N6—H6B⋯Cl1	0.88 (3)	2.66 (3)	3.4552 (18)	150.3 (19)
N6—H6A⋯Cl1^v	0.83 (2)	2.71 (2)	3.4653 (16)	152.9 (19)
N3—H3A⋯Cl1^iv	0.88 (2)	2.59 (2)	3.4075 (17)	154.2 (17)
N3—H3B⋯Cl2ⁱ	0.82 (2)	2.49 (2)	3.2560 (16)	156 (2)
N4—H4A⋯Cl2	0.85 (2)	2.68 (2)	3.5003 (17)	161 (2)
N4—H4B⋯Cl2ⁱⁱⁱ	0.87 (2)	2.55 (2)	3.2919 (16)	143.5 (19)
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z; (iii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (v) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813013135/hb7079sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013135/hb7079Isup2.hkl

checkCIF report

Comment top

In the chiral Co(II)(en)₃ cationic complex (Fig. 1) N atoms form distorted octahedron around central Co atom, cis angles deviate from 90° by less than 10°. Both Λ and Δ isomers are present in equal amounts in the centrosymmetric crystal structure.

Co(en)₃ cationic complexes are stacked in columns along [010] direction (Figure 2) and separated by the columns of Cl anions. There two types of chlorine anions in the crystal structure. Cl1 has distorted octahedral coordination by 6 hydrogen atoms from 4 different Co(en)₃ complexes. Cl2 has distorted trigonal bipyramid coordination by 5 hydrogen atoms from 2 different Co(en)₃ complexes. H···Cl distances vary from 2.45 to 2.70 Å.

The corresponding Co(III) trisethylenediamine complex with chloride counter-anions has been reported. (Takamizawa et al., 2008). The Co(III)(en)₃ cationic complex is more regular: cis angles deviate from 90° by less than 4°.

Related literature top

The corresponding Co^III–tris-ethylenediamine complex with chloride counter-anions has been reported by Takamizawa et al. (2008).

Experimental top

The title compound, [Co(C₂N₂H₈)₃]Cl₂, was obtained unintentionally as the product of an attempted synthesis of cobalt selenide. Co (64 mg), Se (86 mg), and NH₄Cl (100 mg) were reacted in ethylenediamine (en) solvent (30 ml). Reaction was performed in closed hydrothermal vessel at 180°C for 48 h. Degree of the vessel filling was 70%. Irregular moisture-sensitive yellow crystals of the title compound were recovered.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Packing of the molecules in the crystal structure of (I) along (top) [100] and (bottom) [010] crystallographic directions. Cl–H distances in the range from 2.45 to 2.70 Å are shown with dashed lines.

Tris(ethylenediamine)cobalt(II) dichloride' top

Crystal data top

[Co(C₂H₈N₂)₃]Cl₂	D_x = 1.451 Mg m⁻³
M_r = 310.14	Melting point: not measured K
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
a = 8.1590 (8) Å	Cell parameters from 6618 reflections
b = 17.047 (3) Å	θ = 4.3–71.0°
c = 20.3974 (14) Å	µ = 12.81 mm⁻¹
V = 2837.0 (6) Å³	T = 90 K
Z = 8	Irregular, yellow
F(000) = 1304	0.31 × 0.17 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	2700 independent reflections
Radiation source: fine-focus sealed tube	2437 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 72.0°, θ_min = 4.3°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −9→9
T_min = 0.109, T_max = 0.243	k = −19→20
17930 measured reflections	l = −24→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.059	All H-atom parameters refined
S = 1.06	w = 1/[σ²(F_o²) + (0.0273P)² + 1.3198P] where P = (F_o² + 2F_c²)/3
2700 reflections	(Δ/σ)_max = 0.001
232 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Co(C₂H₈N₂)₃]Cl₂	V = 2837.0 (6) Å³
M_r = 310.14	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 8.1590 (8) Å	µ = 12.81 mm⁻¹
b = 17.047 (3) Å	T = 90 K
c = 20.3974 (14) Å	0.31 × 0.17 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	2700 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	2437 reflections with I > 2σ(I)
T_min = 0.109, T_max = 0.243	R_int = 0.042
17930 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.059	All H-atom parameters refined
S = 1.06	Δρ_max = 0.26 e Å⁻³
2700 reflections	Δρ_min = −0.37 e Å⁻³
232 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Co	0.22206 (3)	0.636475 (16)	0.101937 (14)	0.01130 (9)
Cl1	0.22916 (5)	0.38557 (2)	0.02211 (2)	0.01517 (10)
Cl2	0.19514 (5)	0.63342 (2)	0.32464 (2)	0.01878 (11)
N1	0.31525 (19)	0.56644 (9)	0.18154 (8)	0.0144 (3)
H1A	0.419 (3)	0.5613 (12)	0.1780 (10)	0.021 (6)*
H1B	0.297 (3)	0.5888 (15)	0.2164 (12)	0.023 (6)*
N2	0.04364 (19)	0.54264 (9)	0.09943 (8)	0.0155 (3)
H2A	−0.051 (3)	0.5597 (13)	0.0934 (10)	0.019 (6)*
H2B	0.068 (3)	0.5088 (13)	0.0683 (11)	0.023 (6)*
C1	0.2324 (2)	0.48967 (10)	0.18119 (9)	0.0169 (4)
H1C	0.238 (2)	0.4648 (12)	0.2236 (10)	0.014 (5)*
H1D	0.285 (2)	0.4581 (12)	0.1472 (10)	0.016 (5)*
C2	0.0533 (2)	0.50142 (11)	0.16281 (9)	0.0167 (4)
H2C	0.003 (2)	0.5343 (12)	0.1971 (10)	0.020 (5)*
H2D	0.001 (2)	0.4511 (12)	0.1614 (10)	0.018 (5)*
N6	0.37572 (19)	0.57543 (9)	0.03100 (8)	0.0156 (3)
H5B	0.044 (3)	0.6765 (13)	0.0010 (10)	0.023 (6)*
H5A	0.135 (3)	0.7409 (15)	0.0172 (10)	0.024 (6)*
N5	0.14074 (19)	0.69328 (9)	0.01218 (8)	0.0152 (3)
H6A	0.474 (3)	0.5868 (13)	0.0328 (10)	0.020 (5)*
H6B	0.372 (3)	0.5247 (15)	0.0387 (11)	0.029 (6)*
C5	0.2573 (2)	0.67473 (11)	−0.04124 (9)	0.0179 (4)
H5D	0.351 (2)	0.7073 (12)	−0.0344 (9)	0.016 (5)*
H5C	0.211 (2)	0.6829 (13)	−0.0850 (11)	0.021 (5)*
C6	0.3113 (2)	0.59006 (11)	−0.03548 (9)	0.0182 (4)
H6D	0.217 (2)	0.5559 (11)	−0.0402 (9)	0.008 (4)*
H6C	0.391 (3)	0.5790 (12)	−0.0690 (10)	0.019 (5)*
N3	0.38406 (18)	0.73377 (9)	0.12091 (8)	0.0146 (3)
H3A	0.385 (2)	0.7681 (13)	0.0886 (10)	0.016 (5)*
H3B	0.478 (3)	0.7190 (13)	0.1278 (11)	0.023 (6)*
N4	0.07178 (18)	0.70245 (9)	0.17074 (8)	0.0155 (3)
H4B	−0.032 (3)	0.7045 (13)	0.1610 (10)	0.027 (6)*
H4A	0.079 (3)	0.6796 (14)	0.2080 (11)	0.026 (6)*
C3	0.3253 (2)	0.77480 (11)	0.17991 (9)	0.0175 (4)
H3D	0.353 (2)	0.7452 (12)	0.2186 (9)	0.011 (5)*
H3C	0.374 (2)	0.8260 (12)	0.1837 (9)	0.016 (5)*
C4	0.1402 (2)	0.78212 (10)	0.17682 (10)	0.0178 (4)
H4C	0.109 (2)	0.8107 (12)	0.1386 (10)	0.018 (5)*
H4D	0.097 (3)	0.8110 (12)	0.2159 (10)	0.020 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co	0.00953 (15)	0.00972 (15)	0.01465 (16)	−0.00031 (10)	−0.00038 (10)	0.00023 (10)
Cl1	0.0154 (2)	0.0123 (2)	0.0178 (2)	−0.00106 (14)	−0.00053 (15)	0.00024 (15)
Cl2	0.0122 (2)	0.0245 (2)	0.0197 (2)	0.00031 (15)	0.00082 (16)	−0.00254 (17)
N1	0.0125 (8)	0.0140 (7)	0.0166 (8)	0.0004 (6)	−0.0007 (6)	−0.0010 (6)
N2	0.0127 (8)	0.0134 (8)	0.0204 (9)	0.0004 (6)	−0.0011 (6)	−0.0001 (6)
C1	0.0196 (9)	0.0125 (9)	0.0186 (9)	−0.0005 (7)	−0.0005 (7)	0.0022 (7)
C2	0.0176 (9)	0.0119 (8)	0.0207 (10)	−0.0024 (7)	0.0022 (7)	0.0013 (7)
N6	0.0120 (8)	0.0138 (8)	0.0211 (8)	0.0009 (6)	0.0007 (6)	0.0007 (6)
N5	0.0133 (7)	0.0118 (8)	0.0204 (8)	0.0009 (6)	−0.0020 (6)	−0.0005 (6)
C5	0.0184 (9)	0.0175 (9)	0.0177 (10)	−0.0011 (7)	−0.0012 (7)	0.0010 (7)
C6	0.0189 (9)	0.0177 (9)	0.0181 (10)	0.0006 (7)	0.0022 (8)	−0.0030 (7)
N3	0.0114 (7)	0.0136 (7)	0.0189 (8)	−0.0005 (6)	−0.0006 (6)	0.0020 (6)
N4	0.0132 (8)	0.0129 (7)	0.0205 (9)	−0.0011 (6)	0.0019 (6)	0.0000 (6)
C3	0.0201 (9)	0.0125 (9)	0.0198 (10)	−0.0034 (7)	−0.0015 (7)	0.0003 (7)
C4	0.0210 (9)	0.0106 (8)	0.0217 (10)	0.0001 (7)	0.0023 (8)	−0.0001 (7)

Geometric parameters (Å, º) top

Co—N1	2.1540 (15)	N5—C5	1.480 (2)
Co—N3	2.1558 (15)	N5—H5B	0.87 (2)
Co—N2	2.1635 (15)	N5—H5A	0.82 (2)
Co—N5	2.1748 (15)	C5—C6	1.514 (3)
Co—N4	2.1767 (15)	C5—H5D	0.95 (2)
Co—N6	2.1791 (16)	C5—H5C	0.98 (2)
N1—C1	1.473 (2)	C6—H6D	0.967 (19)
N1—H1A	0.86 (2)	C6—H6C	0.96 (2)
N1—H1B	0.82 (2)	N3—C3	1.472 (2)
N2—C2	1.473 (2)	N3—H3A	0.88 (2)
N2—H2A	0.83 (2)	N3—H3B	0.82 (2)
N2—H2B	0.88 (2)	N4—C4	1.474 (2)
C1—C2	1.522 (2)	N4—H4B	0.87 (2)
C1—H1C	0.96 (2)	N4—H4A	0.85 (2)
C1—H1D	0.98 (2)	C3—C4	1.517 (2)
C2—H2C	0.99 (2)	C3—H3D	0.963 (19)
C2—H2D	0.96 (2)	C3—H3C	0.96 (2)
N6—C6	1.475 (2)	C4—H4C	0.95 (2)
N6—H6A	0.83 (2)	C4—H4D	1.00 (2)
N6—H6B	0.88 (3)

N1—Co—N3	94.28 (6)	H6A—N6—H6B	105 (2)
N1—Co—N2	81.11 (6)	C5—N5—Co	109.18 (11)
N3—Co—N2	170.27 (6)	C5—N5—H5B	108.7 (14)
N1—Co—N5	171.51 (6)	Co—N5—H5B	110.5 (14)
N3—Co—N5	89.75 (6)	C5—N5—H5A	109.8 (15)
N2—Co—N5	95.97 (6)	Co—N5—H5A	110.6 (15)
N1—Co—N4	89.95 (6)	H5B—N5—H5A	108 (2)
N3—Co—N4	80.33 (6)	N5—C5—C6	109.49 (15)
N2—Co—N4	91.05 (6)	N5—C5—H5D	106.3 (12)
N5—Co—N4	98.10 (6)	C6—C5—H5D	108.2 (12)
N1—Co—N6	91.88 (6)	N5—C5—H5C	113.1 (12)
N3—Co—N6	97.69 (6)	C6—C5—H5C	108.5 (13)
N2—Co—N6	91.05 (6)	H5D—C5—H5C	111.1 (17)
N5—Co—N6	80.17 (6)	N6—C6—C5	109.64 (15)
N4—Co—N6	177.41 (6)	N6—C6—H6D	105.8 (11)
C1—N1—Co	109.07 (11)	C5—C6—H6D	109.6 (11)
C1—N1—H1A	111.3 (14)	N6—C6—H6C	112.2 (12)
Co—N1—H1A	110.0 (14)	C5—C6—H6C	109.1 (13)
C1—N1—H1B	109.6 (16)	H6D—C6—H6C	110.4 (16)
Co—N1—H1B	109.5 (16)	C3—N3—Co	108.21 (11)
H1A—N1—H1B	107 (2)	C3—N3—H3A	107.4 (13)
C2—N2—Co	107.21 (11)	Co—N3—H3A	112.6 (13)
C2—N2—H2A	110.2 (14)	C3—N3—H3B	108.1 (16)
Co—N2—H2A	111.6 (15)	Co—N3—H3B	111.7 (15)
C2—N2—H2B	108.0 (14)	H3A—N3—H3B	109 (2)
Co—N2—H2B	110.4 (14)	C4—N4—Co	108.49 (11)
H2A—N2—H2B	109 (2)	C4—N4—H4B	110.5 (15)
N1—C1—C2	108.96 (14)	Co—N4—H4B	114.9 (15)
N1—C1—H1C	111.3 (12)	C4—N4—H4A	108.7 (16)
C2—C1—H1C	109.1 (12)	Co—N4—H4A	107.5 (15)
N1—C1—H1D	106.9 (12)	H4B—N4—H4A	107 (2)
C2—C1—H1D	108.7 (11)	N3—C3—C4	109.24 (15)
H1C—C1—H1D	111.9 (16)	N3—C3—H3D	110.2 (11)
N2—C2—C1	109.29 (15)	C4—C3—H3D	108.0 (11)
N2—C2—H2C	109.2 (12)	N3—C3—H3C	111.2 (12)
C1—C2—H2C	107.6 (12)	C4—C3—H3C	110.0 (12)
N2—C2—H2D	112.1 (12)	H3D—C3—H3C	108.2 (16)
C1—C2—H2D	108.4 (12)	N4—C4—C3	107.74 (14)
H2C—C2—H2D	110.2 (17)	N4—C4—H4C	107.6 (12)
C6—N6—Co	108.95 (11)	C3—C4—H4C	109.8 (12)
C6—N6—H6A	110.3 (15)	N4—C4—H4D	112.8 (12)
Co—N6—H6A	114.7 (15)	C3—C4—H4D	110.8 (12)
C6—N6—H6B	108.5 (14)	H4C—C4—H4D	108.0 (16)
Co—N6—H6B	109.3 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Cl2	0.82 (2)	2.48 (3)	3.2839 (17)	167 (2)
N1—H1A···Cl2ⁱ	0.86 (2)	2.57 (2)	3.3056 (16)	145.4 (18)
N2—H2A···Cl1ⁱⁱ	0.83 (2)	2.92 (2)	3.5494 (16)	133.6 (17)
N2—H2A···Cl2ⁱⁱⁱ	0.83 (2)	2.94 (2)	3.5887 (17)	135.8 (17)
N2—H2B···Cl1	0.88 (2)	2.65 (2)	3.4566 (17)	152.5 (18)
N5—H5B···Cl1ⁱⁱ	0.87 (2)	2.51 (2)	3.3770 (16)	173.1 (19)
N5—H5A···Cl1^iv	0.82 (2)	2.70 (2)	3.4514 (18)	152.4 (19)
N6—H6B···Cl1	0.88 (3)	2.66 (3)	3.4552 (18)	150.3 (19)
N6—H6A···Cl1^v	0.83 (2)	2.71 (2)	3.4653 (16)	152.9 (19)
N3—H3A···Cl1^iv	0.88 (2)	2.59 (2)	3.4075 (17)	154.2 (17)
N3—H3B···Cl2ⁱ	0.82 (2)	2.49 (2)	3.2560 (16)	156 (2)
N4—H4A···Cl2	0.85 (2)	2.68 (2)	3.5003 (17)	161 (2)
N4—H4B···Cl2ⁱⁱⁱ	0.87 (2)	2.55 (2)	3.2919 (16)	143.5 (19)

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

Experimental details

Crystal data
Chemical formula	[Co(C₂H₈N₂)₃]Cl₂
M_r	310.14
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	90
a, b, c (Å)	8.1590 (8), 17.047 (3), 20.3974 (14)
V (Å³)	2837.0 (6)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	12.81
Crystal size (mm)	0.31 × 0.17 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.109, 0.243
No. of measured, independent and observed [I > 2σ(I)] reflections	17930, 2700, 2437
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.059, 1.06
No. of reflections	2700
No. of parameters	232
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.37

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).

Selected bond lengths (Å) top

Co—N1	2.1540 (15)	Co—N5	2.1748 (15)
Co—N3	2.1558 (15)	Co—N4	2.1767 (15)
Co—N2	2.1635 (15)	Co—N6	2.1791 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Cl2	0.82 (2)	2.48 (3)	3.2839 (17)	167 (2)
N1—H1A···Cl2ⁱ	0.86 (2)	2.57 (2)	3.3056 (16)	145.4 (18)
N2—H2A···Cl1ⁱⁱ	0.83 (2)	2.92 (2)	3.5494 (16)	133.6 (17)
N2—H2A···Cl2ⁱⁱⁱ	0.83 (2)	2.94 (2)	3.5887 (17)	135.8 (17)
N2—H2B···Cl1	0.88 (2)	2.65 (2)	3.4566 (17)	152.5 (18)
N5—H5B···Cl1ⁱⁱ	0.87 (2)	2.51 (2)	3.3770 (16)	173.1 (19)
N5—H5A···Cl1^iv	0.82 (2)	2.70 (2)	3.4514 (18)	152.4 (19)
N6—H6B···Cl1	0.88 (3)	2.66 (3)	3.4552 (18)	150.3 (19)
N6—H6A···Cl1^v	0.83 (2)	2.71 (2)	3.4653 (16)	152.9 (19)
N3—H3A···Cl1^iv	0.88 (2)	2.59 (2)	3.4075 (17)	154.2 (17)
N3—H3B···Cl2ⁱ	0.82 (2)	2.49 (2)	3.2560 (16)	156 (2)
N4—H4A···Cl2	0.85 (2)	2.68 (2)	3.5003 (17)	161 (2)
N4—H4B···Cl2ⁱⁱⁱ	0.87 (2)	2.55 (2)	3.2919 (16)	143.5 (19)

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

Acknowledgements

The authors thank the UC Davis ChemEnergy NSF REU Grant #CHE-1004925 for financial support.

References

Bruker (2003). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Takamizawa, S., Akatsuka, T. & Ueda, T. (2008). Angew. Chem. Int. Ed. 47, 1689–1692. Web of Science CSD CrossRef CAS Google Scholar