cis-Aqua-chloridobis(1,10-phenanthroline-κN,N')cobalt(II) chloride 2.5-hydrate.

In the title complex, [CoCl(C(12)H(8)N(2))(2)(H(2)O)]Cl·2.5H(2)O, the Co(II) ion is coordinated by four N atoms of two bis-chelating 1,10-phenanthroline (phen) ligands, one water mol-ecule and a chloride ligand in a distorted octa-hedral environment. The dihedral angle between the two phen ligands is 84.21 (3)°. In the crystal structure, complex mol-ecules and chloride ions are linked into centrosymmetric four-component clusters by inter-molecular O-H⋯Cl hydrogen bonds. Of the 2.5 solvent water mol-ecules in the asymmetric unit, two were refined as disordered over two sites with fixed occupancies of ratios 0.50:0.50 and 0.60:0.40, while another was refined with half occupancy.

Related literature

1,10-Phenanthroline is a versatile ligand capable of forming highly stable complexes with transition n class="Chemical">metal ions, see: Nobufumi (1969 ▶). Metal complexes functionalized with 1,10-phenanthrolines have been used as catalyst for the enantio selective hydrolysis of N-protected amino acid esters and in enantio selective reduction of acetophenone, see: Weijnen et al. (1992 ▶). For some examples of the applications of substituted phenanthroline compounds, see Garuti et al. (1989 ▶). For the crystal structures of related cobalt complexes of 1,10-phenanthroline, see: Sun & Feng (2006 ▶); Zhong et al. (2006 ▶). For the crystal structure of the title complex with thio­acetamide solvent rather than water, see: Zhong et al. (2007 ▶). For the use of metal complexes of 1,10-phenanthroline in developing new diagnostic and therapeutic agents that can recognize and cleave DNA, see: Arai et al. (2005 ▶); Müller et al. (1987 ▶). Oxovanadium complexes of dimethyl-substituted phenanthroline will induce apoptosis in human cancer cells, and may be useful for the treatment of cancer, see: Rama Krishna et al. (2000 ▶). Weijnen et al. (1992 ▶); Nobufumi (1969 ▶).

Experimental

Crystal data

[CoCl(C12H8N2)2(H2O)]Cl·2.5H2O

M = 553.29

Triclinic,

a = 9.6597 (3) Å

b = 11.4386 (3) Å

c = 12.9886 (4) Å

α = 64.224 (1)°

β = 86.377 (2)°

γ = 78.303 (1)°

V = 1265.01 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.93 mm−1

T = 293 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.722, T max = 0.812

34458 measured reflections

9683 independent reflections

7380 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.138

S = 1.10

9683 reflections

343 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.72 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038422/lh2895sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038422/lh2895Isup2.hkl

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

[CoCl(C12H8N2)2(H2O)]Cl·2.5H2O	Z = 2
Mr = 553.29	F(000) = 576
Triclinic, P1	Dx = 1.463 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6597 (3) Å	Cell parameters from 7839 reflections
b = 11.4386 (3) Å	θ = 2.7–32.5°
c = 12.9886 (4) Å	µ = 0.93 mm−1
α = 64.224 (1)°	T = 293 K
β = 86.377 (2)°	Plate, red
γ = 78.303 (1)°	0.30 × 0.30 × 0.20 mm
V = 1265.01 (6) Å3

Bruker Kappa APEXII CCD diffractometer	9683 independent reflections
Radiation source: fine-focus sealed tube	7380 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω and φ scans	θmax = 33.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.722, Tmax = 0.812	k = −17→17
34458 measured reflections	l = −19→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0685P)2 + 0.4443P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
9683 reflections	Δρmax = 0.72 e Å−3
343 parameters	Δρmin = −0.42 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0038 (12)

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	Occ. (<1)
C1	0.6979 (2)	0.9429 (3)	0.1406 (2)	0.0498 (5)
H1	0.7847	0.9396	0.1056	0.060*
C2	0.6035 (3)	0.8711 (3)	0.1298 (3)	0.0634 (7)
H2	0.6280	0.8205	0.0891	0.076*
C3	0.4749 (3)	0.8757 (3)	0.1794 (3)	0.0593 (6)
H3	0.4102	0.8295	0.1718	0.071*
C4	0.4415 (2)	0.9510 (2)	0.24212 (18)	0.0413 (4)
C5	0.3106 (2)	0.9586 (2)	0.3001 (2)	0.0485 (5)
H5	0.2420	0.9155	0.2936	0.058*
C6	0.2858 (2)	1.0266 (2)	0.36317 (19)	0.0444 (5)
H6	0.2015	1.0276	0.4019	0.053*
C7	0.38682 (18)	1.09809 (18)	0.37217 (15)	0.0355 (4)
C8	0.3665 (2)	1.1707 (2)	0.43717 (17)	0.0426 (4)
H8	0.2844	1.1737	0.4782	0.051*
C9	0.4674 (2)	1.2367 (2)	0.44004 (18)	0.0436 (4)
H9	0.4545	1.2861	0.4822	0.052*
C10	0.5913 (2)	1.22959 (19)	0.37879 (17)	0.0377 (4)
H10	0.6594	1.2755	0.3810	0.045*
C11	0.51474 (17)	1.09520 (16)	0.31430 (14)	0.0300 (3)
C12	0.54289 (17)	1.01907 (18)	0.24953 (15)	0.0319 (3)
C13	0.9632 (2)	1.2764 (2)	0.31592 (19)	0.0430 (4)
H13	0.9838	1.1955	0.3800	0.052*
C14	1.0192 (3)	1.3822 (3)	0.3113 (3)	0.0567 (6)
H14	1.0759	1.3711	0.3713	0.068*
C15	0.9900 (3)	1.5015 (2)	0.2182 (3)	0.0565 (6)
H15	1.0279	1.5720	0.2137	0.068*
C16	0.9028 (2)	1.5171 (2)	0.1295 (2)	0.0449 (5)
C17	0.8652 (3)	1.6387 (2)	0.0285 (3)	0.0590 (7)
H17	0.9002	1.7123	0.0201	0.071*
C18	0.7806 (3)	1.6483 (2)	−0.0541 (2)	0.0606 (7)
H18	0.7584	1.7283	−0.1188	0.073*
C19	0.7241 (2)	1.5380 (2)	−0.04446 (18)	0.0460 (5)
C20	0.6344 (3)	1.5425 (3)	−0.1270 (2)	0.0594 (7)
H20	0.6094	1.6204	−0.1933	0.071*
C21	0.5838 (3)	1.4333 (3)	−0.1105 (2)	0.0579 (6)
H21	0.5228	1.4362	−0.1644	0.069*
C22	0.6249 (2)	1.3163 (2)	−0.01098 (18)	0.0444 (4)
H22	0.5913	1.2415	−0.0009	0.053*
C23	0.75899 (18)	1.41697 (17)	0.05320 (15)	0.0334 (3)
C24	0.85017 (18)	1.40623 (17)	0.14098 (16)	0.0334 (3)
O2'	0.6535 (14)	0.3986 (11)	0.6280 (11)	0.195 (6)	0.40
O2	0.3871 (11)	0.4705 (7)	0.6502 (7)	0.190 (4)	0.60
O3	0.9469 (11)	0.3167 (6)	0.6132 (6)	0.125 (3)	0.50
O3'	1.0826 (15)	0.2976 (8)	0.6422 (8)	0.180 (5)	0.50
O4	1.1914 (12)	0.4501 (10)	0.5278 (7)	0.171 (4)	0.50
N1	0.66940 (16)	1.01569 (16)	0.19855 (14)	0.0350 (3)
N2	0.61525 (15)	1.16040 (14)	0.31806 (12)	0.0299 (3)
N3	0.88180 (15)	1.28706 (15)	0.23231 (13)	0.0319 (3)
N4	0.70912 (16)	1.30782 (15)	0.06895 (13)	0.0329 (3)
O1	0.95884 (15)	1.10031 (14)	0.11464 (12)	0.0382 (3)
Cl1	0.92546 (5)	0.95686 (5)	0.38472 (4)	0.03919 (11)
Cl2	0.88362 (6)	0.18004 (6)	0.86264 (5)	0.04968 (13)
Co1	0.79827 (2)	1.13428 (2)	0.222016 (18)	0.02766 (7)
H1A	1.006 (3)	1.0167 (13)	0.138 (2)	0.062 (8)*
H1B	0.930 (3)	1.129 (3)	0.0417 (11)	0.058 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0438 (11)	0.0636 (14)	0.0639 (14)	−0.0216 (10)	0.0158 (10)	−0.0447 (12)
C2	0.0605 (14)	0.0834 (18)	0.0834 (19)	−0.0336 (13)	0.0197 (13)	−0.0640 (17)
C3	0.0521 (13)	0.0754 (17)	0.0757 (17)	−0.0336 (12)	0.0103 (12)	−0.0476 (15)
C4	0.0346 (9)	0.0504 (11)	0.0434 (10)	−0.0180 (8)	0.0024 (7)	−0.0203 (9)
C5	0.0328 (9)	0.0598 (13)	0.0524 (12)	−0.0216 (9)	0.0032 (8)	−0.0187 (10)
C6	0.0258 (8)	0.0540 (11)	0.0452 (11)	−0.0110 (7)	0.0057 (7)	−0.0134 (9)
C7	0.0270 (7)	0.0379 (8)	0.0308 (8)	−0.0038 (6)	0.0030 (6)	−0.0062 (7)
C8	0.0337 (9)	0.0462 (10)	0.0366 (9)	−0.0005 (7)	0.0083 (7)	−0.0114 (8)
C9	0.0455 (10)	0.0461 (10)	0.0385 (10)	−0.0022 (8)	0.0072 (8)	−0.0212 (8)
C10	0.0383 (9)	0.0393 (9)	0.0371 (9)	−0.0065 (7)	0.0037 (7)	−0.0188 (7)
C11	0.0253 (7)	0.0319 (7)	0.0263 (7)	−0.0047 (5)	0.0001 (5)	−0.0069 (6)
C12	0.0270 (7)	0.0362 (8)	0.0313 (8)	−0.0094 (6)	0.0004 (6)	−0.0119 (6)
C13	0.0411 (10)	0.0462 (10)	0.0478 (11)	−0.0080 (8)	−0.0065 (8)	−0.0251 (9)
C14	0.0518 (12)	0.0613 (14)	0.0757 (17)	−0.0144 (11)	−0.0087 (11)	−0.0440 (13)
C15	0.0506 (12)	0.0496 (12)	0.0876 (18)	−0.0215 (10)	0.0092 (12)	−0.0424 (13)
C16	0.0410 (10)	0.0345 (9)	0.0619 (13)	−0.0133 (7)	0.0157 (9)	−0.0226 (9)
C17	0.0592 (14)	0.0306 (9)	0.0793 (18)	−0.0159 (9)	0.0251 (13)	−0.0165 (10)
C18	0.0700 (16)	0.0306 (9)	0.0575 (14)	−0.0056 (9)	0.0199 (12)	−0.0016 (9)
C19	0.0458 (10)	0.0358 (9)	0.0371 (10)	0.0030 (8)	0.0101 (8)	−0.0040 (7)
C20	0.0609 (14)	0.0527 (13)	0.0353 (10)	0.0138 (11)	−0.0021 (10)	−0.0023 (9)
C21	0.0543 (13)	0.0698 (16)	0.0361 (10)	0.0118 (12)	−0.0160 (9)	−0.0184 (11)
C22	0.0410 (10)	0.0521 (11)	0.0378 (10)	0.0014 (8)	−0.0075 (8)	−0.0206 (9)
C23	0.0313 (8)	0.0306 (7)	0.0312 (8)	−0.0017 (6)	0.0070 (6)	−0.0094 (6)
C24	0.0306 (7)	0.0305 (7)	0.0386 (9)	−0.0075 (6)	0.0086 (6)	−0.0149 (7)
O2'	0.207 (12)	0.110 (7)	0.169 (10)	−0.002 (7)	0.033 (9)	0.015 (7)
O2	0.282 (10)	0.100 (5)	0.180 (7)	−0.020 (5)	−0.061 (7)	−0.051 (5)
O3	0.238 (9)	0.059 (3)	0.062 (3)	−0.024 (5)	0.029 (5)	−0.017 (2)
O3'	0.349 (16)	0.074 (5)	0.123 (7)	−0.049 (8)	0.064 (9)	−0.053 (5)
O4	0.242 (10)	0.192 (9)	0.128 (6)	−0.078 (8)	0.062 (7)	−0.107 (7)
N1	0.0306 (7)	0.0418 (8)	0.0396 (8)	−0.0130 (6)	0.0071 (6)	−0.0221 (7)
N2	0.0283 (6)	0.0313 (6)	0.0281 (6)	−0.0055 (5)	0.0021 (5)	−0.0114 (5)
N3	0.0306 (7)	0.0323 (7)	0.0332 (7)	−0.0076 (5)	0.0009 (5)	−0.0138 (6)
N4	0.0329 (7)	0.0350 (7)	0.0289 (7)	−0.0032 (5)	0.0017 (5)	−0.0137 (6)
O1	0.0384 (7)	0.0389 (7)	0.0338 (7)	−0.0044 (5)	0.0073 (5)	−0.0147 (5)
Cl1	0.0372 (2)	0.0397 (2)	0.0311 (2)	−0.00573 (16)	−0.00006 (16)	−0.00724 (16)
Cl2	0.0557 (3)	0.0504 (3)	0.0480 (3)	−0.0067 (2)	0.0007 (2)	−0.0273 (2)
Co1	0.02642 (11)	0.02914 (11)	0.02756 (12)	−0.00822 (8)	0.00243 (8)	−0.01140 (8)

C1—N1	1.328 (3)	C14—H14	0.9300
C1—C2	1.394 (3)	C15—C16	1.397 (4)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.365 (4)	C16—C24	1.406 (3)
C2—H2	0.9300	C16—C17	1.433 (3)
C3—C4	1.405 (3)	C17—C18	1.343 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C12	1.401 (2)	C18—C19	1.428 (4)
C4—C5	1.437 (3)	C18—H18	0.9300
C5—C6	1.338 (3)	C19—C20	1.397 (4)
C5—H5	0.9300	C19—C23	1.406 (3)
C6—C7	1.434 (3)	C20—C21	1.359 (4)
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.401 (3)	C21—C22	1.401 (3)
C7—C11	1.407 (2)	C21—H21	0.9300
C8—C9	1.360 (3)	C22—N4	1.318 (3)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.403 (3)	C23—N4	1.357 (2)
C9—H9	0.9300	C23—C24	1.432 (3)
C10—N2	1.322 (2)	C24—N3	1.353 (2)
C10—H10	0.9300	N1—Co1	2.1389 (15)
C11—N2	1.354 (2)	N2—Co1	2.1453 (14)
C11—C12	1.432 (3)	N3—Co1	2.1241 (15)
C12—N1	1.354 (2)	N4—Co1	2.1738 (15)
C13—N3	1.329 (2)	O1—Co1	2.1108 (13)
C13—C14	1.398 (3)	O1—H1A	0.896 (10)
C13—H13	0.9300	O1—H1B	0.898 (10)
C14—C15	1.363 (4)	Cl1—Co1	2.3835 (5)
N1—C1—C2	122.9 (2)	C17—C18—C19	121.3 (2)
N1—C1—H1	118.5	C17—C18—H18	119.4
C2—C1—H1	118.5	C19—C18—H18	119.4
C3—C2—C1	119.5 (2)	C20—C19—C23	117.1 (2)
C3—C2—H2	120.2	C20—C19—C18	123.8 (2)
C1—C2—H2	120.2	C23—C19—C18	119.1 (2)
C2—C3—C4	119.1 (2)	C21—C20—C19	120.1 (2)
C2—C3—H3	120.5	C21—C20—H20	120.0
C4—C3—H3	120.5	C19—C20—H20	120.0
C12—C4—C3	117.69 (18)	C20—C21—C22	119.1 (2)
C12—C4—C5	119.22 (19)	C20—C21—H21	120.4
C3—C4—C5	123.07 (19)	C22—C21—H21	120.4
C6—C5—C4	121.13 (18)	N4—C22—C21	122.7 (2)
C6—C5—H5	119.4	N4—C22—H22	118.6
C4—C5—H5	119.4	C21—C22—H22	118.6
C5—C6—C7	121.14 (18)	N4—C23—C19	122.64 (19)
C5—C6—H6	119.4	N4—C23—C24	117.64 (15)
C7—C6—H6	119.4	C19—C23—C24	119.72 (18)
C8—C7—C11	117.27 (17)	N3—C24—C16	122.97 (19)
C8—C7—C6	123.58 (17)	N3—C24—C23	117.24 (15)
C11—C7—C6	119.15 (18)	C16—C24—C23	119.78 (18)
C9—C8—C7	119.68 (17)	C1—N1—C12	117.90 (16)
C9—C8—H8	120.2	C1—N1—Co1	128.30 (13)
C7—C8—H8	120.2	C12—N1—Co1	113.80 (12)
C8—C9—C10	119.29 (19)	C10—N2—C11	118.18 (15)
C8—C9—H9	120.4	C10—N2—Co1	128.29 (13)
C10—C9—H9	120.4	C11—N2—Co1	113.53 (11)
N2—C10—C9	122.77 (19)	C13—N3—C24	117.96 (16)
N2—C10—H10	118.6	C13—N3—Co1	127.18 (13)
C9—C10—H10	118.6	C24—N3—Co1	114.83 (12)
N2—C11—C7	122.79 (17)	C22—N4—C23	118.33 (17)
N2—C11—C12	117.62 (14)	C22—N4—Co1	128.70 (14)
C7—C11—C12	119.59 (16)	C23—N4—Co1	112.74 (12)
N1—C12—C4	122.85 (17)	Co1—O1—H1A	116.3 (19)
N1—C12—C11	117.43 (15)	Co1—O1—H1B	114.6 (18)
C4—C12—C11	119.72 (16)	H1A—O1—H1B	107 (3)
N3—C13—C14	122.6 (2)	O1—Co1—N3	93.44 (6)
N3—C13—H13	118.7	O1—Co1—N1	94.48 (6)
C14—C13—H13	118.7	N3—Co1—N1	166.38 (6)
C15—C14—C13	119.6 (2)	O1—Co1—N2	171.52 (6)
C15—C14—H14	120.2	N3—Co1—N2	93.79 (6)
C13—C14—H14	120.2	N1—Co1—N2	77.58 (6)
C14—C15—C16	119.52 (19)	O1—Co1—N4	85.36 (5)
C14—C15—H15	120.2	N3—Co1—N4	77.19 (6)
C16—C15—H15	120.2	N1—Co1—N4	92.42 (6)
C15—C16—C24	117.4 (2)	N2—Co1—N4	91.91 (5)
C15—C16—C17	123.7 (2)	O1—Co1—Cl1	90.18 (4)
C24—C16—C17	118.9 (2)	N3—Co1—Cl1	96.39 (4)
C18—C17—C16	121.3 (2)	N1—Co1—Cl1	94.66 (5)
C18—C17—H17	119.4	N2—Co1—Cl1	93.43 (4)
C16—C17—H17	119.4	N4—Co1—Cl1	171.92 (4)
N1—C1—C2—C3	0.7 (5)	C9—C10—N2—Co1	−178.68 (14)
C1—C2—C3—C4	−1.1 (5)	C7—C11—N2—C10	−0.1 (2)
C2—C3—C4—C12	0.6 (4)	C12—C11—N2—C10	−179.13 (16)
C2—C3—C4—C5	−178.1 (3)	C7—C11—N2—Co1	179.45 (13)
C12—C4—C5—C6	−1.8 (3)	C12—C11—N2—Co1	0.39 (18)
C3—C4—C5—C6	176.9 (2)	C14—C13—N3—C24	−1.5 (3)
C4—C5—C6—C7	2.1 (3)	C14—C13—N3—Co1	176.37 (17)
C5—C6—C7—C8	−179.9 (2)	C16—C24—N3—C13	1.9 (3)
C5—C6—C7—C11	−0.6 (3)	C23—C24—N3—C13	−178.24 (17)
C11—C7—C8—C9	1.4 (3)	C16—C24—N3—Co1	−176.25 (14)
C6—C7—C8—C9	−179.36 (19)	C23—C24—N3—Co1	3.6 (2)
C7—C8—C9—C10	−0.8 (3)	C21—C22—N4—C23	−0.7 (3)
C8—C9—C10—N2	−0.3 (3)	C21—C22—N4—Co1	−174.82 (17)
C8—C7—C11—N2	−1.0 (3)	C19—C23—N4—C22	0.1 (3)
C6—C7—C11—N2	179.73 (16)	C24—C23—N4—C22	179.86 (17)
C8—C7—C11—C12	178.05 (16)	C19—C23—N4—Co1	175.15 (14)
C6—C7—C11—C12	−1.2 (3)	C24—C23—N4—Co1	−5.10 (19)
C3—C4—C12—N1	0.5 (3)	C13—N3—Co1—O1	−98.21 (17)
C5—C4—C12—N1	179.22 (19)	C24—N3—Co1—O1	79.76 (12)
C3—C4—C12—C11	−178.9 (2)	C13—N3—Co1—N1	136.3 (2)
C5—C4—C12—C11	−0.1 (3)	C24—N3—Co1—N1	−45.7 (3)
N2—C11—C12—N1	1.3 (2)	C13—N3—Co1—N2	86.24 (17)
C7—C11—C12—N1	−177.80 (16)	C24—N3—Co1—N2	−95.79 (12)
N2—C11—C12—C4	−179.35 (17)	C13—N3—Co1—N4	177.34 (17)
C7—C11—C12—C4	1.6 (3)	C24—N3—Co1—N4	−4.69 (12)
N3—C13—C14—C15	0.1 (4)	C13—N3—Co1—Cl1	−7.64 (17)
C13—C14—C15—C16	1.0 (4)	C24—N3—Co1—Cl1	170.32 (12)
C14—C15—C16—C24	−0.7 (3)	C1—N1—Co1—O1	4.1 (2)
C14—C15—C16—C17	179.6 (2)	C12—N1—Co1—O1	−175.11 (13)
C15—C16—C17—C18	−179.8 (2)	C1—N1—Co1—N3	129.5 (3)
C24—C16—C17—C18	0.4 (3)	C12—N1—Co1—N3	−49.7 (3)
C16—C17—C18—C19	0.3 (4)	C1—N1—Co1—N2	−179.0 (2)
C17—C18—C19—C20	179.3 (2)	C12—N1—Co1—N2	1.85 (13)
C17—C18—C19—C23	−0.5 (3)	C1—N1—Co1—N4	89.6 (2)
C23—C19—C20—C21	0.6 (3)	C12—N1—Co1—N4	−89.58 (13)
C18—C19—C20—C21	−179.1 (2)	C1—N1—Co1—Cl1	−86.5 (2)
C19—C20—C21—C22	−1.1 (4)	C12—N1—Co1—Cl1	94.34 (13)
C20—C21—C22—N4	1.2 (4)	C10—N2—Co1—O1	−160.7 (3)
C20—C19—C23—N4	−0.1 (3)	C11—N2—Co1—O1	19.8 (4)
C18—C19—C23—N4	179.69 (18)	C10—N2—Co1—N3	−12.39 (16)
C20—C19—C23—C24	−179.81 (18)	C11—N2—Co1—N3	168.16 (12)
C18—C19—C23—C24	−0.1 (3)	C10—N2—Co1—N1	178.27 (17)
C15—C16—C24—N3	−0.8 (3)	C11—N2—Co1—N1	−1.18 (11)
C17—C16—C24—N3	178.91 (19)	C10—N2—Co1—N4	−89.67 (16)
C15—C16—C24—C23	179.33 (18)	C11—N2—Co1—N4	90.87 (12)
C17—C16—C24—C23	−0.9 (3)	C10—N2—Co1—Cl1	84.26 (15)
N4—C23—C24—N3	1.1 (2)	C11—N2—Co1—Cl1	−95.20 (11)
C19—C23—C24—N3	−179.10 (16)	C22—N4—Co1—O1	85.00 (17)
N4—C23—C24—C16	−179.01 (16)	C23—N4—Co1—O1	−89.41 (12)
C19—C23—C24—C16	0.7 (3)	C22—N4—Co1—N3	179.59 (18)
C2—C1—N1—C12	0.3 (4)	C23—N4—Co1—N3	5.19 (11)
C2—C1—N1—Co1	−178.9 (2)	C22—N4—Co1—N1	−9.31 (17)
C4—C12—N1—C1	−0.9 (3)	C23—N4—Co1—N1	176.29 (12)
C11—C12—N1—C1	178.44 (19)	C22—N4—Co1—N2	−86.96 (17)
C4—C12—N1—Co1	178.38 (15)	C23—N4—Co1—N2	98.64 (12)
C11—C12—N1—Co1	−2.3 (2)	C22—N4—Co1—Cl1	141.7 (3)
C9—C10—N2—C11	0.7 (3)	C23—N4—Co1—Cl1	−32.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl2i	0.90 (2)	2.29 (2)	3.1530 (18)	162 (2)
O1—H1B···Cl2ii	0.90 (2)	2.19 (2)	3.0836 (15)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Cl2i	0.90 (2)	2.290 (19)	3.1530 (18)	162 (2)
O1—H1B⋯Cl2ii	0.90 (2)	2.190 (16)	3.0836 (15)	173 (3)

Symmetry codes: (i) ; (ii) .