(μ(2)-Chlorido)-(μ(2)-pyridine-2-carboxyl-ato-1:2κN,O:O)-dichlorido(ethanol-κO)bis-[N-hy-droxy-1-(pyridin-2-yl)methan-imine-κ(2)N,N']dicobalt(II).

The dinuclear title compound, [Co(2)Cl(3)(C(6)H(4)NO(2))(C(6)H(6)N(2)O)(2)(C(2)H(5)OH)], contains two six-coordinate Co(II) atoms with different octa-hedral coordination environments. One Co(II) atom is coordinated by two N atoms from one pyridine-2-carbaldehyde oxime ligand, by one terminal and one bridging Cl(-) ion, by one O atom from an ethanol mol-ecule, and by one O atom from a bridging pyridine-2-carboxyl-ate (picolinate) anion. The second Co(II) atom is coordinated by two N atoms from another pyridine-2-carbaldehyde oxime ligand, one N and one O atom from the bridging picolinate anion, and by one terminal Cl(-) and one bridging Cl(-) anion. The structure displays intra-molecular O-H⋯O and O-H⋯Cl hydrogen bonds. Weak C-H⋯Cl hydrogen-bonding inter-actions connect the mol-ecules into a three-dimensional network.

Related literature

For examples of CoII complexes with pyridine-2-carbaldehyde oxime ligands, see: Stamatatos et al. (2005a ▶,b ▶, 2009 ▶); Ross et al. (2001 ▶). For the isostructural NiII analogue, see: Zheng et al. (2011 ▶).

Experimental

Crystal data

[Co2Cl3(C6H4NO2)(C6H6N2O)2(C2H6O)]

M = 636.64

Monoclinic,

a = 8.7443 (17) Å

b = 18.144 (4) Å

c = 16.643 (3) Å

β = 99.23 (3)°

V = 2606.4 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.62 mm−1

T = 293 K

0.30 × 0.25 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.642, T max = 0.727

17261 measured reflections

4520 independent reflections

3778 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.165

S = 1.18

4520 reflections

319 parameters

14 restraints

H-atom parameters constrained

Δρmax = 1.09 e Å−3

Δρmin = −1.31 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812041736/wm2687sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041736/wm2687Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Co2Cl3(C6H4NO2)(C6H6N2O)2(C2H6O)]	F(000) = 1288
Mr = 636.64	char
Monoclinic, P21/c	Dx = 1.622 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.7443 (17) Å	Cell parameters from 3510 reflections
b = 18.144 (4) Å	θ = 2.6–25.3°
c = 16.643 (3) Å	µ = 1.62 mm−1
β = 99.23 (3)°	T = 293 K
V = 2606.4 (9) Å3	Block, brown
Z = 4	0.30 × 0.25 × 0.21 mm

Bruker APEXII CCD diffractometer	4520 independent reflections
Radiation source: fine-focus sealed tube	3778 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→7
Tmin = 0.642, Tmax = 0.727	k = −21→17
17261 measured reflections	l = −18→19

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
4520 reflections	(Δ/σ)max = 0.035
319 parameters	Δρmax = 1.09 e Å−3
14 restraints	Δρmin = −1.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
Co1	0.24774 (6)	0.45656 (2)	0.21872 (3)	0.0402 (2)
O3	0.2615 (3)	0.34808 (12)	0.26096 (15)	0.0431 (5)
Co2	0.14638 (5)	0.27859 (2)	0.16890 (3)	0.0375 (2)
N1	0.2554 (3)	0.56337 (14)	0.16917 (18)	0.0390 (7)
Cl3	0.08768 (10)	0.39748 (4)	0.09972 (5)	0.0428 (3)
N5	0.1902 (3)	0.20948 (15)	0.27256 (18)	0.0405 (7)
Cl4	0.38894 (10)	0.25504 (5)	0.12436 (5)	0.0446 (3)
N2	0.4077 (4)	0.51273 (17)	0.3068 (2)	0.0532 (8)
Cl5	0.04241 (13)	0.47676 (5)	0.29287 (7)	0.0599 (3)
C13	0.2646 (4)	0.24129 (18)	0.3398 (2)	0.0422 (8)
C5	0.1754 (4)	0.58864 (19)	0.1008 (2)	0.0452 (8)
H5	0.1081	0.5569	0.0686	0.054*
O5	0.4324 (4)	0.42495 (16)	0.1587 (2)	0.0755 (9)
H5A	0.4181	0.3816	0.1395	0.091*
N3	0.0182 (4)	0.20307 (16)	0.0874 (2)	0.0474 (7)
C17	0.1477 (5)	0.13908 (19)	0.2775 (3)	0.0499 (9)
H17	0.0967	0.1159	0.2309	0.060*
N4	−0.0840 (4)	0.28758 (17)	0.1948 (2)	0.0508 (8)
C6	0.4351 (5)	0.5793 (2)	0.2900 (3)	0.0539 (10)
H6	0.5061	0.6073	0.3248	0.065*
C1	0.3537 (4)	0.61002 (19)	0.2159 (2)	0.0436 (8)
C2	0.3710 (5)	0.6820 (2)	0.1930 (3)	0.0533 (10)
H2	0.4399	0.7130	0.2253	0.064*
C18	0.3098 (5)	0.32080 (19)	0.3299 (2)	0.0473 (7)
O4	0.3859 (5)	0.35214 (16)	0.3880 (2)	0.0806 (10)
O2	−0.1396 (4)	0.33138 (18)	0.2505 (2)	0.0702 (9)
H2A	−0.0851	0.3682	0.2592	0.105*
C14	0.2986 (5)	0.2054 (2)	0.4128 (2)	0.0534 (10)
H14	0.3518	0.2291	0.4585	0.064*
C11	0.0707 (6)	0.1604 (2)	0.0337 (3)	0.0619 (11)
H11	0.1747	0.1640	0.0285	0.074*
O1	0.4862 (5)	0.48710 (18)	0.3784 (2)	0.0836 (11)
H1	0.4460	0.4488	0.3908	0.125*
C15	0.2517 (5)	0.1328 (2)	0.4166 (3)	0.0560 (11)
H15	0.2716	0.1069	0.4655	0.067*
C7	−0.1329 (5)	0.1977 (2)	0.0940 (3)	0.0527 (10)
C16	0.1765 (5)	0.0998 (2)	0.3486 (3)	0.0546 (10)
H16	0.1448	0.0510	0.3502	0.065*
C3	0.2871 (6)	0.7074 (2)	0.1233 (3)	0.0618 (12)
H3	0.2966	0.7563	0.1080	0.074*
C4	0.1879 (5)	0.6610 (2)	0.0751 (3)	0.0572 (10)
H4	0.1304	0.6776	0.0266	0.069*
C19	0.5751 (6)	0.4495 (3)	0.1537 (4)	0.0872 (12)
H19A	0.6444	0.4338	0.2021	0.105*
H19B	0.5732	0.5029	0.1539	0.105*
C12	−0.1848 (5)	0.2464 (2)	0.1537 (3)	0.0571 (11)
H12	−0.2878	0.2473	0.1613	0.068*
C8	−0.2318 (6)	0.1499 (3)	0.0475 (3)	0.0752 (14)
H8	−0.3356	0.1474	0.0535	0.090*
C10	−0.0215 (7)	0.1106 (3)	−0.0154 (3)	0.0793 (15)
H10	0.0197	0.0812	−0.0524	0.095*
C20	0.6395 (7)	0.4247 (3)	0.0818 (4)	0.0869 (17)
H20A	0.6291	0.3722	0.0766	0.130*
H20B	0.7471	0.4379	0.0879	0.130*
H20C	0.5842	0.4479	0.0339	0.130*
C9	−0.1751 (7)	0.1058 (3)	−0.0078 (4)	0.0886 (17)
H9	−0.2401	0.0730	−0.0399	0.106*

	U11	U22	U33	U12	U13	U23
Co1	0.0441 (3)	0.0344 (3)	0.0410 (3)	−0.00033 (19)	0.0033 (3)	−0.00025 (17)
O3	0.0526 (13)	0.0361 (11)	0.0379 (12)	0.0020 (10)	−0.0012 (11)	0.0034 (9)
Co2	0.0386 (3)	0.0373 (3)	0.0360 (3)	−0.00170 (18)	0.0039 (3)	0.00143 (17)
N1	0.0405 (16)	0.0351 (13)	0.0410 (17)	−0.0009 (12)	0.0053 (14)	−0.0003 (12)
Cl3	0.0450 (5)	0.0427 (5)	0.0389 (5)	−0.0019 (4)	0.0013 (4)	0.0037 (3)
N5	0.0423 (16)	0.0403 (14)	0.0388 (17)	0.0020 (12)	0.0059 (14)	0.0061 (12)
Cl4	0.0408 (5)	0.0464 (5)	0.0470 (6)	0.0052 (4)	0.0082 (4)	−0.0003 (4)
N2	0.060 (2)	0.0443 (17)	0.049 (2)	−0.0008 (15)	−0.0098 (17)	0.0022 (14)
Cl5	0.0740 (7)	0.0520 (5)	0.0591 (7)	0.0109 (5)	0.0272 (6)	0.0026 (4)
C13	0.050 (2)	0.0398 (16)	0.038 (2)	0.0077 (16)	0.0088 (18)	0.0047 (14)
C5	0.046 (2)	0.0465 (18)	0.041 (2)	−0.0026 (16)	0.0009 (18)	−0.0007 (15)
O5	0.0564 (16)	0.0550 (15)	0.124 (3)	−0.0128 (13)	0.0415 (18)	−0.0243 (16)
N3	0.0502 (19)	0.0450 (15)	0.0437 (18)	−0.0074 (14)	−0.0024 (16)	0.0040 (13)
C17	0.054 (2)	0.0426 (19)	0.053 (2)	−0.0017 (17)	0.007 (2)	0.0066 (16)
N4	0.0475 (19)	0.0470 (16)	0.061 (2)	0.0025 (15)	0.0181 (18)	0.0093 (15)
C6	0.061 (2)	0.0441 (19)	0.052 (2)	−0.0105 (18)	−0.004 (2)	−0.0081 (17)
C1	0.044 (2)	0.0435 (18)	0.043 (2)	−0.0015 (15)	0.0060 (17)	−0.0062 (15)
C2	0.063 (2)	0.0456 (19)	0.051 (2)	−0.0122 (18)	0.007 (2)	−0.0038 (17)
C18	0.0573 (18)	0.0397 (15)	0.0412 (16)	0.0055 (14)	−0.0031 (16)	0.0011 (13)
O4	0.128 (3)	0.0466 (15)	0.0528 (19)	−0.0108 (18)	−0.029 (2)	0.0031 (13)
O2	0.0638 (19)	0.0657 (19)	0.088 (2)	0.0002 (15)	0.0337 (19)	−0.0059 (16)
C14	0.067 (3)	0.055 (2)	0.039 (2)	0.0097 (19)	0.009 (2)	0.0035 (16)
C11	0.071 (3)	0.059 (2)	0.055 (3)	−0.009 (2)	0.008 (2)	−0.0079 (19)
O1	0.108 (3)	0.0595 (19)	0.066 (2)	−0.0138 (18)	−0.037 (2)	0.0093 (15)
C15	0.070 (3)	0.053 (2)	0.049 (2)	0.008 (2)	0.020 (2)	0.0179 (18)
C7	0.047 (2)	0.053 (2)	0.055 (3)	−0.0141 (18)	−0.002 (2)	0.0151 (18)
C16	0.056 (2)	0.049 (2)	0.060 (3)	0.0027 (18)	0.016 (2)	0.0178 (18)
C3	0.082 (3)	0.0406 (19)	0.062 (3)	−0.008 (2)	0.009 (3)	0.0075 (19)
C4	0.068 (3)	0.048 (2)	0.052 (2)	−0.001 (2)	−0.001 (2)	0.0091 (17)
C19	0.062 (2)	0.077 (2)	0.130 (3)	−0.0157 (18)	0.038 (2)	−0.028 (2)
C12	0.039 (2)	0.060 (2)	0.073 (3)	−0.0074 (19)	0.011 (2)	0.013 (2)
C8	0.064 (3)	0.078 (3)	0.078 (3)	−0.027 (3)	−0.007 (3)	0.006 (3)
C10	0.104 (4)	0.068 (3)	0.063 (3)	−0.021 (3)	0.005 (3)	−0.020 (2)
C20	0.082 (4)	0.077 (3)	0.112 (5)	−0.012 (3)	0.048 (4)	−0.013 (3)
C9	0.099 (4)	0.077 (3)	0.079 (4)	−0.040 (3)	−0.018 (3)	−0.004 (3)

Co1—O3	2.087 (2)	C6—H6	0.9300
Co1—O5	2.110 (3)	C1—C2	1.376 (5)
Co1—N1	2.111 (3)	C2—C3	1.350 (6)
Co1—N2	2.118 (4)	C2—H2	0.9300
Co1—Cl5	2.3648 (11)	C18—O4	1.223 (5)
Co1—Cl3	2.4781 (12)	O2—H2A	0.8200
O3—C18	1.258 (4)	C14—C15	1.384 (5)
O3—Co2	2.111 (3)	C14—H14	0.9300
Co2—N3	2.118 (3)	C11—C10	1.388 (7)
Co2—N5	2.117 (3)	C11—H11	0.9300
Co2—N4	2.133 (3)	O1—H1	0.8200
Co2—Cl4	2.3948 (10)	C15—C16	1.354 (6)
Co2—Cl3	2.4603 (10)	C15—H15	0.9300
N1—C5	1.319 (5)	C7—C8	1.372 (6)
N1—C1	1.358 (5)	C7—C12	1.455 (6)
N5—C17	1.337 (4)	C16—H16	0.9300
N5—C13	1.333 (5)	C3—C4	1.371 (6)
N2—C6	1.271 (5)	C3—H3	0.9300
N2—O1	1.359 (5)	C4—H4	0.9300
C13—C14	1.369 (5)	C19—C20	1.473 (7)
C13—C18	1.512 (5)	C19—H19A	0.9700
C5—C4	1.391 (5)	C19—H19B	0.9700
C5—H5	0.9300	C12—H12	0.9300
O5—C19	1.339 (5)	C8—C9	1.371 (8)
O5—H5A	0.8499	C8—H8	0.9300
N3—C11	1.319 (5)	C10—C9	1.371 (8)
N3—C7	1.347 (5)	C10—H10	0.9300
C17—C16	1.370 (6)	C20—H20A	0.9600
C17—H17	0.9300	C20—H20B	0.9600
N4—C12	1.269 (6)	C20—H20C	0.9600
N4—O2	1.368 (4)	C9—H9	0.9300
C6—C1	1.435 (6)
O3—Co1—O5	84.04 (11)	O2—N4—Co2	129.1 (3)
O3—Co1—N1	173.45 (10)	N2—C6—C1	118.2 (4)
O5—Co1—N1	89.42 (12)	N2—C6—H6	120.9
O3—Co1—N2	102.98 (11)	C1—C6—H6	120.9
O5—Co1—N2	89.32 (14)	N1—C1—C2	121.4 (4)
N1—Co1—N2	76.69 (12)	N1—C1—C6	115.5 (3)
O3—Co1—Cl5	88.74 (7)	C2—C1—C6	123.1 (4)
O5—Co1—Cl5	172.77 (9)	C3—C2—C1	119.5 (4)
N1—Co1—Cl5	97.81 (8)	C3—C2—H2	120.2
N2—Co1—Cl5	92.09 (10)	C1—C2—H2	120.2
O3—Co1—Cl3	81.72 (7)	O4—C18—O3	126.8 (3)
O5—Co1—Cl3	83.16 (10)	O4—C18—C13	118.4 (3)
N1—Co1—Cl3	97.71 (9)	O3—C18—C13	114.8 (3)
N2—Co1—Cl3	170.71 (10)	N4—O2—H2A	109.5
Cl5—Co1—Cl3	96.05 (4)	C13—C14—C15	118.0 (4)
C18—O3—Co1	132.1 (2)	C13—C14—H14	121.0
C18—O3—Co2	118.5 (2)	C15—C14—H14	121.0
Co1—O3—Co2	108.89 (11)	N3—C11—C10	123.3 (4)
O3—Co2—N3	173.23 (10)	N3—C11—H11	118.3
O3—Co2—N5	76.08 (11)	C10—C11—H11	118.3
N3—Co2—N5	98.43 (12)	N2—O1—H1	109.5
O3—Co2—N4	99.41 (12)	C16—C15—C14	119.3 (4)
N3—Co2—N4	76.05 (13)	C16—C15—H15	120.3
N5—Co2—N4	86.20 (12)	C14—C15—H15	120.3
O3—Co2—Cl4	89.33 (7)	N3—C7—C8	122.5 (4)
N3—Co2—Cl4	95.19 (9)	N3—C7—C12	115.4 (4)
N5—Co2—Cl4	95.35 (8)	C8—C7—C12	122.1 (4)
N4—Co2—Cl4	171.24 (10)	C15—C16—C17	119.3 (4)
O3—Co2—Cl3	81.68 (7)	C15—C16—H16	120.3
N3—Co2—Cl3	102.62 (9)	C17—C16—H16	120.3
N5—Co2—Cl3	153.82 (8)	C2—C3—C4	119.9 (4)
N4—Co2—Cl3	83.95 (9)	C2—C3—H3	120.0
Cl4—Co2—Cl3	98.06 (3)	C4—C3—H3	120.0
C5—N1—C1	118.5 (3)	C3—C4—C5	118.2 (4)
C5—N1—Co1	127.6 (2)	C3—C4—H4	120.9
C1—N1—Co1	113.9 (2)	C5—C4—H4	120.9
Co2—Cl3—Co1	87.51 (4)	O5—C19—C20	115.5 (5)
C17—N5—C13	117.7 (3)	O5—C19—H19A	108.4
C17—N5—Co2	126.9 (3)	C20—C19—H19A	108.4
C13—N5—Co2	115.3 (2)	O5—C19—H19B	108.4
C6—N2—O1	115.6 (4)	C20—C19—H19B	108.4
C6—N2—Co1	115.6 (3)	H19A—C19—H19B	107.5
O1—N2—Co1	128.9 (2)	N4—C12—C7	117.4 (4)
N5—C13—C14	123.2 (3)	N4—C12—H12	121.3
N5—C13—C18	115.0 (3)	C7—C12—H12	121.3
C14—C13—C18	121.9 (4)	C9—C8—C7	119.0 (5)
N1—C5—C4	122.5 (4)	C9—C8—H8	120.5
N1—C5—H5	118.8	C7—C8—H8	120.5
C4—C5—H5	118.8	C9—C10—C11	118.1 (5)
C19—O5—Co1	136.9 (3)	C9—C10—H10	120.9
C19—O5—H5A	111.5	C11—C10—H10	120.9
Co1—O5—H5A	110.5	C19—C20—H20A	109.5
C11—N3—C7	117.7 (4)	C19—C20—H20B	109.5
C11—N3—Co2	127.4 (3)	H20A—C20—H20B	109.5
C7—N3—Co2	114.8 (3)	C19—C20—H20C	109.5
N5—C17—C16	122.4 (4)	H20A—C20—H20C	109.5
N5—C17—H17	118.8	H20B—C20—H20C	109.5
C16—C17—H17	118.8	C10—C9—C8	119.3 (5)
C12—N4—O2	114.6 (3)	C10—C9—H9	120.3
C12—N4—Co2	116.3 (3)	C8—C9—H9	120.3
O5—Co1—O3—C18	107.7 (3)	N5—Co2—N3—C11	−95.8 (4)
N2—Co1—O3—C18	19.8 (3)	N4—Co2—N3—C11	−179.7 (4)
Cl5—Co1—O3—C18	−72.1 (3)	Cl4—Co2—N3—C11	0.4 (3)
Cl3—Co1—O3—C18	−168.4 (3)	Cl3—Co2—N3—C11	99.9 (3)
O5—Co1—O3—Co2	−80.18 (14)	N5—Co2—N3—C7	82.3 (3)
N2—Co1—O3—Co2	−168.10 (12)	N4—Co2—N3—C7	−1.6 (3)
Cl5—Co1—O3—Co2	100.04 (10)	Cl4—Co2—N3—C7	178.5 (3)
Cl3—Co1—O3—Co2	3.74 (8)	Cl3—Co2—N3—C7	−82.0 (3)
C18—O3—Co2—N5	3.5 (3)	C13—N5—C17—C16	0.8 (5)
Co1—O3—Co2—N5	−169.85 (13)	Co2—N5—C17—C16	−177.4 (3)
C18—O3—Co2—N4	87.2 (3)	O3—Co2—N4—C12	−174.2 (3)
Co1—O3—Co2—N4	−86.18 (13)	N3—Co2—N4—C12	0.7 (3)
C18—O3—Co2—Cl4	−92.2 (3)	N5—Co2—N4—C12	−99.0 (3)
Co1—O3—Co2—Cl4	94.47 (9)	Cl3—Co2—N4—C12	105.3 (3)
C18—O3—Co2—Cl3	169.6 (3)	O3—Co2—N4—O2	5.2 (3)
Co1—O3—Co2—Cl3	−3.77 (8)	N3—Co2—N4—O2	−179.9 (3)
O5—Co1—N1—C5	92.3 (3)	N5—Co2—N4—O2	80.4 (3)
N2—Co1—N1—C5	−178.2 (3)	Cl3—Co2—N4—O2	−75.3 (3)
Cl5—Co1—N1—C5	−87.9 (3)	O1—N2—C6—C1	−178.9 (3)
Cl3—Co1—N1—C5	9.3 (3)	Co1—N2—C6—C1	1.8 (5)
O5—Co1—N1—C1	−88.9 (2)	C5—N1—C1—C2	−0.3 (5)
N2—Co1—N1—C1	0.5 (2)	Co1—N1—C1—C2	−179.1 (3)
Cl5—Co1—N1—C1	90.8 (2)	C5—N1—C1—C6	179.0 (3)
Cl3—Co1—N1—C1	−171.9 (2)	Co1—N1—C1—C6	0.2 (4)
O3—Co2—Cl3—Co1	3.01 (7)	N2—C6—C1—N1	−1.3 (5)
N3—Co2—Cl3—Co1	177.68 (9)	N2—C6—C1—C2	178.0 (4)
N5—Co2—Cl3—Co1	35.0 (2)	N1—C1—C2—C3	1.0 (6)
N4—Co2—Cl3—Co1	103.47 (11)	C6—C1—C2—C3	−178.3 (4)
Cl4—Co2—Cl3—Co1	−85.12 (4)	Co1—O3—C18—O4	−12.9 (6)
O3—Co1—Cl3—Co2	−3.04 (7)	Co2—O3—C18—O4	175.5 (4)
O5—Co1—Cl3—Co2	81.89 (10)	Co1—O3—C18—C13	166.0 (2)
N1—Co1—Cl3—Co2	170.37 (8)	Co2—O3—C18—C13	−5.5 (4)
Cl5—Co1—Cl3—Co2	−90.87 (4)	N5—C13—C18—O4	−176.1 (4)
O3—Co2—N5—C17	177.6 (3)	C14—C13—C18—O4	3.9 (6)
N3—Co2—N5—C17	1.7 (3)	N5—C13—C18—O3	4.9 (5)
N4—Co2—N5—C17	76.9 (3)	C14—C13—C18—O3	−175.2 (3)
Cl4—Co2—N5—C17	−94.4 (3)	N5—C13—C14—C15	−0.7 (6)
Cl3—Co2—N5—C17	145.0 (2)	C18—C13—C14—C15	179.4 (3)
O3—Co2—N5—C13	−0.5 (2)	C7—N3—C11—C10	−0.4 (7)
N3—Co2—N5—C13	−176.5 (2)	Co2—N3—C11—C10	177.7 (4)
N4—Co2—N5—C13	−101.2 (3)	C13—C14—C15—C16	0.9 (6)
Cl4—Co2—N5—C13	87.4 (2)	C11—N3—C7—C8	0.2 (6)
Cl3—Co2—N5—C13	−33.2 (4)	Co2—N3—C7—C8	−178.1 (3)
O3—Co1—N2—C6	172.0 (3)	C11—N3—C7—C12	−179.5 (4)
O5—Co1—N2—C6	88.3 (3)	Co2—N3—C7—C12	2.2 (4)
N1—Co1—N2—C6	−1.2 (3)	C14—C15—C16—C17	−0.4 (6)
Cl5—Co1—N2—C6	−98.8 (3)	N5—C17—C16—C15	−0.5 (6)
O3—Co1—N2—O1	−7.2 (4)	C1—C2—C3—C4	−1.3 (6)
O5—Co1—N2—O1	−90.9 (4)	C2—C3—C4—C5	0.9 (6)
N1—Co1—N2—O1	179.5 (4)	N1—C5—C4—C3	−0.2 (6)
Cl5—Co1—N2—O1	82.0 (4)	Co1—O5—C19—C20	−158.8 (4)
C17—N5—C13—C14	−0.2 (5)	O2—N4—C12—C7	−179.2 (3)
Co2—N5—C13—C14	178.2 (3)	Co2—N4—C12—C7	0.3 (5)
C17—N5—C13—C18	179.8 (3)	N3—C7—C12—N4	−1.7 (6)
Co2—N5—C13—C18	−1.9 (4)	C8—C7—C12—N4	178.7 (4)
C1—N1—C5—C4	−0.1 (5)	N3—C7—C8—C9	0.0 (7)
Co1—N1—C5—C4	178.6 (3)	C12—C7—C8—C9	179.6 (5)
O3—Co1—O5—C19	−126.6 (6)	N3—C11—C10—C9	0.4 (8)
N1—Co1—O5—C19	53.2 (6)	C11—C10—C9—C8	−0.2 (8)
N2—Co1—O5—C19	−23.5 (6)	C7—C8—C9—C10	0.0 (8)
Cl3—Co1—O5—C19	151.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···Cl5	0.82	2.29	3.103 (3)	172
O1—H1···O4	0.82	1.83	2.615 (4)	160
O5—H5A···Cl4	0.85	2.32	3.147 (3)	164
C12—H12···Cl4i	0.93	2.80	3.684 (4)	160
C10—H10···Cl5ii	0.93	2.82	3.684 (5)	156
C14—H14···Cl4iii	0.93	2.74	3.556 (4)	147
C2—H2···Cl4iv	0.93	2.81	3.654 (5)	152
C17—H17···Cl5v	0.93	2.80	3.491 (4)	132

Table 1

Selected bond lengths (Å)

Co1—O3	2.087 (2)
Co1—O5	2.110 (3)
Co1—N1	2.111 (3)
Co1—N2	2.118 (4)
Co1—Cl5	2.3648 (11)
Co1—Cl3	2.4781 (12)
O3—Co2	2.111 (3)
Co2—N3	2.118 (3)
Co2—N5	2.117 (3)
Co2—N4	2.133 (3)
Co2—Cl4	2.3948 (10)
Co2—Cl3	2.4603 (10)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯Cl5	0.82	2.29	3.103 (3)	172
O1—H1⋯O4	0.82	1.83	2.615 (4)	160
O5—H5A⋯Cl4	0.85	2.32	3.147 (3)	164
C12—H12⋯Cl4i	0.93	2.80	3.684 (4)	160
C10—H10⋯Cl5ii	0.93	2.82	3.684 (5)	156
C14—H14⋯Cl4iii	0.93	2.74	3.556 (4)	147
C2—H2⋯Cl4iv	0.93	2.81	3.654 (5)	152
C17—H17⋯Cl5v	0.93	2.80	3.491 (4)	132

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .